The Future Of Work Demands New Organizational Design

How remote work, social entrepreneurship, and the sharing economy are colliding to drive us towards community based, self-managed organizations

By Geoff Roberts

I’ve written previously about how we’re embracing self-management as we build Outseta. Frederic Laloux’s book Reinventing Organizations has had a significant influence on how we want to build and operate our company, as evidenced by our open sourced operating agreement which details how we make financial and functional decisions at Outseta. 

But to most of the world of SaaS self-management remains an abstract concept, most often known only as an organizational structure that Zappos has adopted with mixed results if not dismissed altogether. Even to me, self-management has always felt a bit ahead of its time.

On a personal level, I’ve been struggling as of late to find that “next thing” to write about that hasn’t already been beaten to death in the world of SaaS start-ups. As SaaS has matured, the industry’s playbook has become well understood and I’ve found myself relentlessly bombarded by the same messages:

  • Pricing should be based on value

  • Retention is a growth strategy

  • Transparency is great (but it’s now largely table stakes)

  • Meditation helps keep us balanced

  • Drift is scaling a reality TV show 

This isn’t a dig at any of these topics—all good things—but it’s been a long time since I’ve heard many truly new, fresh perspectives in the world of tech. 

I recently read Better Work Together, a collection of stories published by the Enspiral Foundation, and it presented self-management in an entirely new light for me. The book presents self-management as a method of organizational design that we’re rapidly hurtling towards, driven by a series of trends that we all agree are already making up the so-called future of work:

  1. Remote work and digital nomadism

  2. Social entrepreneurship

  3. Transparency

  4. The open source and decentralization movements

Taken collectively, where are these trends leading us? That’s what this post is all about and I think I may have stumbled upon the “next big thing” that I was looking for—even if the tech world isn’t quite ready for it.

Tech world, meet Enspiral

Chances are you haven’t heard of Enspiral—despite the fact that I’m building a self-managed company I hadn’t until recently. In short, they’re an interesting organization because they’ve already traveled to the furthest reaches of the future of work—Better Work Together is their report back on what the future holds.

For the past decade Enspiral has been “a community of entrepreneurs experimenting at the edges of ownership, governance, decision making, resource sharing, and educational design.”

More tactically, Enspiral started as a loose collaboration of freelancers supporting one another and sharing resources in New Zealand back in 2008. The group was brought together largely by social entrepreneurship—their mantra is “More people working on stuff that matters. If your primary mission is to make the world a better place, your personal success is the reason Enspiral exists.” 

In the early days Enspiral members kept 80% of their earnings, choosing to contribute 20% to Enspiral, a shared governing body for the collective. In the decade since this has evolved into an ecosystem of people and companies connected through a co-owned hub, now called Enspiral Foundation.

Enspiral itself is a self-managed organization without any hierarchy, but the lack of hierarchy itself is not what’s interesting to me about self-management. What I think is powerful and compelling about this book (and self-management in general) is the idea that entrepreneurs can take greater, bolder risks and be more successful when they choose to work on their own projects and companies but with the backing of a community rather than operating purely independently. 

What I think is powerful and compelling about self-management is the idea that entrepreneurs can take greater, bolder risks and be more successful when they choose to work on their own projects and companies but with the backing of a community rather than operating purely independently.

“That’s just the way the game works,” says Susan Basterfield, an Enspiral member. “Bosses have ‘their people’ and human resources decides who is worth how much. Most of us willingly go along with this. It’s a game that we know the rules of. I played along for another few years. Then I stopped. Being supported and challenged as an entrepreneur inside a community was a breakthrough for me.”

As the prevalence of remote work has grown, I’ve witnessed first hand many entrepreneurs choosing to turn to communities to fulfill their needs for comradeship, belonging, and support throughout their entrepreneurial journeys. We all need a tribe and we’re already actively seeking out and building our own. This is not a new concept, but I think you’ll see this trend evolve rapidly in the coming years.

What I see in Enspiral is a bunch of corporate astronauts, collectively 10 years ahead on a journey that many of us are just—often unknowingly—starting now.

Enspiral’s approach to self management

What struck me as I read Better Work Together was how reasonable the authors were in presenting their case for self-management—it was as far from “Bosses are bad! Let’s be counterculture!” as you could possibly imagine. 

Kate Beecroft provides the definition of self-management that resonates most with me.

Self-management is an approach to work that prioritizes autonomy and self-development alongside alignment with others. 

That sounds great to me—that’s a future of work that I want to help build. But while self-management emphasizes autonomy, community-based support systems play an important enabling role in the organizational design needed to make self-management work. 

“Enspiral itself is not producing deliberate external outcomes,” says Chelsea Robinson, an Enspiral member. “The most direct units of impact are the projects that people organize themselves around. However, the community is a very important primordial soup for increasing everybody’s capacity for impact. This is the essence of becoming a platform for impact: combine passionate people, a trickle of money, high risk tolerance, and good intentions.”

Communities then are two main things—cultural echo chambers and accelerators. Here are some of the lessons that Enspiral has learned along the way with regards to how to leverage and build these communities, supported here by short excerpts from the book.

No one organizational structure fits all

“I believe that the right organizational structure is unique to its context, people, objectives, and history.” -Richard D. Bartlett, Co-founder of Loomio

All of which is to say self-management is not a fit for every organization, although most would benefit from the additional space for creativity and agility that self-management provides. SaaS companies—where work largely occurs in front of a laptop and often independently—are a particularly good fit for self-management. But even amongst self-managed organizations, the actual structures and processes used to operate a business may vary widely. 

Management remains necessary

“We need management, not managers. Even though the role of the manager may be redundant, the function of management—of tasks, work, and people—is still needed. This function can take the form of coaching, guiding, and supporting, rather than coercion or direct power from a job title. It comes down to how people can be supported to manage themselves and develop the skills they need, rather than relying on someone to tell them what to do.” -Enspiral member

True equality will never be achieved

“Equality is a compass point to navigate towards, not a destination I’ve ever arrived at. Imbalance can be bad, e.g. inherited privilege, coercion, manipulation, the ‘old boys club.’ Some imbalance can be good: earned trust, reputation, eldership. Transparency reduces toxicity.” -Richard D. Bartlett, Co-founder of Loomio

“We want to exercise power with others, not over others. No one should lead all the time and everyone should lead some of the time.” -Enspiral member

I don’t believe you can (or would want to) have a flat community where everyone is equal in every way. Instead aim for a conscious community where asymmetries are spoken about and consciously managed.
— Joshua Vial, Co-founder of Enspiral Dev Academy

Influence is earned, not assigned

“We’ve learned to distinguish between the coercive power that someone holds over another person, and the social power that someone has earned from their contributions to a group over time. In a ‘Do-ocracy’ power and responsibility accrues to those who execute.” -Francesca Pick, Co-founder of Greatherthan

Ultimately these ideas all boil down to power structures and how they can be applied more effectively to benefit a business. The key idea coming out of Enspiral is that decision making power and ownership should be shared among those doing the work.

These new power dynamics are not ideals that should be quickly discarded, easily cast off as belonging to some group of corporate radicals who are probably sewing hemp shoes in a far off forest in New Zealand. In fact, these same ideas are being discussed in business publications as well known and respected as Harvard Business Review.

Hierarchy is the distance between people making decisions and the people affected by those decisions. We’re talking about reducing that distance. Ideally, there would be no distance at all.
— Enspiral Member

Now let’s turn our attention to the ways in which many of us in SaaS are already starting to work this way, oftentimes without consciously realizing it.

Entrepreneurs are already seeking out community based support groups

As I was reading about Enspiral’s journey, it struck me that this whole “self-management thing” should be a lot less controversial than how it’s often perceived. In fact, as I thought about the world of start-up SaaS companies that I work in I realized that the ideals that Enspiral is advocating for are ones that most of us are starting to reach for already. A few examples:


IndieHackers is a community owned by Stripe, but at its core it’s a community of 45,000+ entrepreneurs supporting one another, sharing ideas, and celebrating milestones together.


Don’t get me wrong, Tinyseed is dressed up as an alternative form of start-up financing and there’s a financial end goal for all involved, but at its core this is a supportive community more than anything else. Founder Rob Walling also founded MicroConf, a conference for self-funded software entrepreneurs. He made friends within this community, was looking for a better way to support those entrepreneurs, and realized that collectively they were more powerful than they’d be individually. 

Tinyseed also recruited a long list of big name mentors for the program to further this idea—collectively 1+1 = 5. While Tinyseed does prodive a small amount of funding to its portfolio companies, I would argue that the community will ultimately make a much larger impact on these companies than the actual financing that Tinyseed provides.

MegaMaker Club

Justin Jackson’s MegaMaker club is a pay-to-play Slack community of entrepreneurs sharing ideas and supporting one another. Like Tinyseed, it’s also a built in amplification channel for its members—anytime Justin publishes a new blog post or podcast, he has a built in community that helps him get the word out. In my conversation with other group members several have expressed that they chose to join the group because they needed a sense of community and a support system that they didn’t have as remote entrepreneurs working independently.

Simply put, as the prevalence of remote work and entrepreneurship has grown more people have realized the need for a tribe—the communities mentioned above are all an example of those tribes being formed. While groups like these aren’t all sharing an organizational structure, ownership, and profits it’s undeniable that they’re communities of individuals with shared values who have recognized that by supporting one another they’re much more powerful than they’d be on their own. They can continue to work on their own projects and interests and leverage the community to increase their chances of success. That’s the very same concept that drove the formation of Enspiral.

How this all ties back to Outseta—and the future of work

When I first read Reinventing Organizations, there were three aspects of the book that really spoke to me. Three years into building Outseta, here are my personal reflections on the importance of each.


As I said, I have no problem with hierarchy but I have seen it cause unhealthy power dynamics and I simply believe that there’s the potential to do better. Anthony Cabraal writes in Better Work Together, “In a company built through transactional relationships people move on when the money stops coming in or a better offer comes along. Any why shouldn’t they? In an industrial economic model we are just rational units of labour, framed by job descriptions, making self interested decisions.”

While that’s a bit harsh for my tastes, it’s at least worthy of contemplation. Personally, I see in self-management an organizational structure that I think will result in more engaged employees more than anything else.

Another of the essays states, “Organizations that best engage and grow talented, caring people will do the best over time.” I agree wholeheartedly and see self-management as a means towards this end.

Bringing your “whole self” to work

Popularly discussed as “vulnerability,” this is the idea that most of us only bring only a small portion of our true selves to work—most often the part of us that’s very masculine, confident, and rational. We check our vulnerabilities, emotions, and uncertainties at the door because we’re afraid that they’ll hurt us in the workplace. 

Laloux’s book proposes that this is actually doing yourself and your company a disservice—a fact supported by the report What Makes A Team At Google Effective? In the report, researchers found that the single most important dynamic of successful teams at Google is psychological safety. 

“Can I express my opinions and be heard? Can I share the challenges I am facing, both personally and professionally, and be supported? Is there space for vulnerability? Can we take risks in this team without feeling insecure of embarrassed?

To me this boils down largely to the benefits of transparency and telling the “full truth.” If you’re constantly putting up a facade that hides your vulnerabilities or concerns, you’re robbing others of the opportunity to help you address them. By doing so you’re simply not giving your organization the best chance to be successful.

Evolutionary purpose

Evolutionary purpose is the idea that the purpose and work that an organization does can evolve over time. You should follow the current to where the collective energy of the group wants to go, and members of self-managed companies will be brought together by shared purpose, values, and ideals.

Reading Better Work Together was a great opportunity for me to reflect on our purpose and why I’ve decided to spend the last three years building Outseta. Dave, Dimitris, and I were certainly brought together by purpose. We want to show that self-management is a viable method of building a business that has benefits in spades over the predominant means of building companies. Silvia Zuur, Director of PwC New Zealand, writes in Better Work Together, “We need to look forward and define the leadership of the future, instead of perpetrating patterns from the past.” I agree.

Additionally, our founding team wants to build software that helps other entrepreneurs succeed with their own start-ups. Both of these purposes still ring true and very much drive the work that we do today.

It’s worth noting that while a shared purpose and philosophical alignment brought our team together, as individuals we all have different purposes, needs, and motivations driving our work too—and that’s perfectly OK! When I think of individual purpose and what we’re each trying to get out of our work at Outseta I can’t help but think of Maslow’s Hierarchy of Needs. Only once you’ve fulfilled your lower level needs and purpose can you move on to the latter stages, and I think that’s true with our team. Said another way, evolutionary purpose occurs at the individual level too.


For example, Dimitris has had more financial success than me—he Co-founded Buildium and because of the company’s financial success his family is taken care of financially. This has allowed him to move up the hierarchy of purpose pyramid, and think more about how Outseta can be used as a vehicle to make the world a better place. He’s also more passionate about building great software than I am—he cares deeply about providing other entrepreneurs with fantastic software tools.

I care about both of these things too, but they don’t drive my individual purpose at this stage of my life to the extent that they do Dimitris’. Financially, I’ve yet to achieve the financial security that he has so it’s more important to me that Outseta helps provide financial security for my family. And building great software is not as powerful of a driver for me—but building a company that provides fantastic job opportunities to others is. My career and life have already benefited tremendously from working in forward thinking organizations, and I’m deeply motivated by the opportunity to provide similar opportunities to others.  

“What if your company was designed from the ground up to challenge and support you to be the best possible version or yourself?” writes Anthony Cabraal. I want Outseta to be an enabler that allows other individuals and their families to live fantastic lives on their own terms—that’s a big part of my individual purpose. 

Closing Thoughts

My objective with this article was not to push any “woo-woo” organizational structure on you or sell you on the need to build a self-managed business. But Enspiral has been challenging the status quo for over a decade, and I think it’s undeniable that there are trends like remote work, the sharing economy, and social entrepreneurship that are driving us towards a place where we should be rethinking our organizational structures.

We’re already seeing entrepreneurs proactively seek out their own tribes—groups that share a common purpose and values where the community itself can be a major catalyst of both personal and professional growth. At the very least I hope that I’ve spurred your own thinking about the structure of your team or start-up, and that you’re open to the idea that self-management could represent a way of Better Work Together.

A Better Approach To Start-up Hiring

Start-ups offer employers and job candidates a unique opportunity to create win-win working relationships

By Geoff Roberts

I have long been a vocal advocate for the importance of Human Resources—ahem, People Operations these days. In a start-up of any sort of scale I’d go so far as to say it’s the single most important function in the company; if you get the right people on the bus you can achieve just about anything.

While that’s the case, it’s always bothered me that there’s often so much apprehension around the hiring process—both from the perspective of the hiring company and the job seeker. For employers, hiring full-time employees means shelling out some serious cash for salary and benefits—people are almost always the single biggest expense for SaaS companies. A mis-hire is not only an expensive mistake, but can also represent a major setback in terms of building your product, hitting your sales number, or properly supporting your customers.

The hiring process is even worse from the perspective of the job applicant. Candidates spend countless hours trying to proactively anticipate interview questions and craft the “right” response. The entire process is often nerve wracking and a vast majority of people feel at least some semblance of imposter syndrome, often disqualifying themselves from positions they’re perfectly capable of fulfilling.

Having sat on both sides of the table, I’ve developed a stupid simple approach to start-up hiring that’s helped me cut through the bullshit on both sides, removing any semblance of smoke and mirrors from the hiring process. This approach has helped me both hire better people and land better job opportunities myself.

How I developed this approach to start-up hiring

I want to start by sharing a few stories that have shaped my perspective on hiring. The first dates back to May 2009, shortly after I graduated with a freshly minted MBA degree. I went to grad school immediately following my undergrad, so I’d never had a “real job” when I graduated. Regardless, I was eager to flex my new degree… except in May of 2009 the economy was in a tailspin. The starting salary of the average graduate from my MBA program the year prior was about $90,000—for my graduating class that dipped down to about $50,000.

Refusing to accept defeat and move home to live with my parents, I drove to Boston one day and took a job waiting tables at Legal Seafoods. The restaurant manager, Myles, looked me square in the eye during the interview and said, “You just graduated with a MBA. Why exactly are you applying to Legal Seafoods?”

I hoped my time waiting tables would be short lived, but I ended up delivering bowls of clam chowder for a solid nine months as I interviewed at companies throughout Boston. One day interviewed at a fitness club where I was asked how much I could bench press, and the next I interviewed at one of the most prestigious consulting firms in Boston where they asked me how many ping-pong balls would fit in the room I was sitting in—before telling me I had only 30 seconds to answer. 

A ping pong ball is about 1 square inch…. This room is about 8x10….”

In retrospect all of those interviews were one of the best things that’s ever happened to my career—I got a ton of practice with interviewing and I learned the important lesson that job interviews are really interviews going both ways  

Eventually I found myself sitting across the table from a start-up CEO, Michael, in an interview where I thought I was doing pretty well. That is until he asked me a final question…

“So what do you know about SEO?”

The truth was I’d just graduated with a MBA focused in marketing, yet I knew absolutely nothing about SEO other than it was an acronym for Search Engine Optimization. I hesitated as my mind waivered on how to respond—”what’s the right answer to this question?” I wondered to myself. When the silence in the room had become deafening I finally blurted something out.

“I don’t know anything about SEO, but if you give me another interview I’ll learn everything I can and will talk you through what my SEO strategy would be for your company when we meet next.”

To my surprise I got the job and learned another important lesson in the process—when it comes to interviewing for jobs, the truth will set you free.  

Fast forward five years, and things at that start-up had gone really well. I was leading a team of 15, the company was growing like a weed, and I loved the people that I was working with. But around that time I was approached by a recruiter and presented with a job opportunity that was hard to ignore. It was my first VP position. It was at a Sequoia company. I was offered a $70,000+ raise. And next thing I knew Mark Roberge, Hubspot’s CRO and a board member at the company, was calling me telling me it was a great opportunity for my career and he’d be excited to work with me.

While I was very happy at my current job, I had some serious student debt—the extra cash would go a long way in paying that off. And after 5 years at my current company I felt like I had been working on the same problem for some time and would benefit from diversifying my professional experience a bit.

At the time it was easily the most difficult professional decision I’d had to make. I wanted to take the new job, but I also knew I had a great job already and was sitting on something of a winning lottery ticket. My existing company was doing very well, had raised funding with very favorable terms, and was a known commodity. The new role was with a company that had a higher risk profile—it was definitely less of a sure thing.

As I hemmed and hawed over the decision, I called Beth Harrison, an executive coach that had been hired to work with our leadership team. She heard me out, then said something profound.

“Geoff, it sounds like you want to take the new job but are worried about the new company being a bit more risky. Why don’t you ask for a parachute?”


Beth proposed that I negotiate by asking for a severance package in order to make the new job a bit less risky—if it didn’t work out I’d at least get paid for a few months while I looked for a new role. I almost choked I was laughing so hard at her suggestion.

A severance package? Come on. I’m 28… no one’s giving me a severance package.

“You’ll never know unless you ask,” Beth insisted. 

I got the severance package and I accepted the new position, learning another key lesson in the process—you’re never going to get what you want unless you’re willing to ask for it.

Start-ups Offer A Unique Opportunity For Us To Be Better To Each Other—Both As Employees and Employers

Since these formative experiences early in my career I’ve gone on to spend a good portion of my time consulting, which means I’ve had a bunch of additional opportunities to apply, pitch, and negotiate employment opportunities at start-up companies. I’ve read countless articles on both hiring and interviewing tips, the vast majority of which I’ve rejected under the same pretense—they make it seem like the hiring process is a game of playing cat and mouse.

I remember reading one article authored by an executive at a well known SaaS company, where he said he would go into a room to interview a candidate and specifically leave some trash on the table. He’d then return later to see if the candidate had thrown the trash out—the idea being this was some sort of barometer for how well candidates take initiative. While I saw the logic, I couldn’t help but think, “This is the type of hiring bullshit I want no part of. This is jumping through hoops.” 

There also seems to be this notion that if you get offered a job, you need to negotiate to absolutely maximize your salary. But you’re then pitted against a hiring manager who is tasked with making stellar hires and bringing them in at 20% under the market rate. So who wins in this scenario?

What I’ve come to understand and appreciate about both hiring and interviewing within start-ups is that you have an enormous amount of freedom to create a win-win situation for both parties involved. Free from the shackles of big company bureaucracy, tiered salaries, and rigid employee handbooks here’s my can’t miss approach to start-up hiring. 

Start-up hiring guidelines for job seekers

Here’s my advice to anyone looking to land a job in a start-up.

Apply to a small number of jobs that you actually want

This is job searching 101, but I have to start with it—the biggest mistake I see people make when they apply for jobs is sending out a large volume of resumes to any job that seems remotely interesting to them. This almost never works; instead, I encourage people to find just three jobs that they’re really excited about and are reasonably qualified for. Go all-in on those applications—make it your singular goal to be the absolute best, most prepared candidate for each of those three roles. If you truly do this, more often than not you’ll get one of the three positions.

This is also very true—but tends to pertain to higher level roles.

This is also very true—but tends to pertain to higher level roles.

Do the sample project when asked

If you’re asked during the interview process to provide a work sample—whether that’s writing some code, delivering a design concept, or sharing a 90-day growth plan—you should do it. I know this is controversial to many people, mostly because you’re being asked to provide value for free but also because it’s time consuming.

Well, if you’re only applying to a small number of positions the time commitment issue flies out the window. And if you’re worried about providing value for free, check your ego at the door. You wouldn’t buy a car without test driving it—why would a company shell out tens or hundreds of thousands of dollars to hire you without getting some insight into how you would be to work with? It’s your job to win the gig, so if you really want the job do the work and over-deliver. 

The correct answer is always the exact truth

Each month I mentor a student or two that’s going through Springboard’s Digital Marketing Career Track, and I hear the same sentiment over and over.

“Geoff, I’m applying for this job at a digital marketing agency. I don’t have much experience with Facebook Ads so what do I say in the interview when they ask me about that?”

My answer is always the same and always surprising to the student—”tell them that!” The point here is not to talk yourself out of a job, but if you say you have experience that you don’t that will very quickly be discovered on the job.

Instead, admit the experiences and skills that you don’t have and mention other experiences that are related and relevant. This could be as simple as, “I haven’t managed Facebook Ads, but I’ve ran some campaigns in Google Ads so I understand paid advertising metrics like cost-per-click. I’d love to learn more about Facebook Ads and think I could pick it up pretty quickly.”

Hiring managers at great companies don’t expect you to have every single desirable skill or experience—your honesty will often be seen as refreshing and totally appropriate.

Ask for what you want

If you’re lucky enough to get a job offer, ask for what you want. It’s really that stupidly simple and you will never know unless you ask. This does not mean that you should be asking for $250,000 salary if you’re applying to an entry level position—you need to have an understanding of your market value and what’s reasonable to ask for, but that aside you should be forthcoming with what it would take to make you really excited to accept the position.

Maybe it’s a $20,000 raise, or a bigger equity stake, or the ability to work from home two days per week. Whatever it is, figure out what’s most important to you and give the hiring company the opportunity to make you a happy camper. It’s always better to negotiate up front than to accept an offer you’re less than excited about only to find yourself asking for a change shortly thereafter.

Share your decision criteria and information on other job offers transparently

If you’re lucky enough to have a couple of job offers on the table, I’d advocate strongly that you share with both companies the fact that you have multiple offers— as well as the criteria that you’ll be using to base your decision on. If that’s money, fine. If it’s title, so be it. If it’s remote flexibility, that’s perfectly OK too. The reason to do this is that you’re going to end up turning somebody down that wanted to hire you. If they at least understand what criteria you used to make your decision—and they see that you took the job most in-line with those criteria—they will understand why you chose to turn them down. Being transparent like this will keep you from burning bridges. 

Perhaps even more controversial, I’d advocate for sharing the details of your other offers transparently. I wouldn’t advocate for doing this proactively, but if you’re asked about your other offers I think it’s totally appropriate to share that information. This shouldn’t be done with the intent of creating a bidding war, but you can do this to show how the offers on the table differ from one another—again you’ve already shared the criteria you’ll be using to make your decision so this is useful context for both hiring parties. The only way you’ll get yourself in trouble here is if you make a decision that goes against the criteria you shared with each company.

Do your diligence on the company

Again this one sounds like a no-brainer, but I mean this at a much deeper level than “read the company’s website and have some questions lined up.” Particularly for more senior roles, part of understanding what’s reasonable to ask for is understanding the stage that the company you’re applying to is at and what the company’s financial situation looks like. 

Has the company raised funding? What’s the company’s current burn rate? You’re probably not going to ask for that $200,000 salary in a company that’s doing $500,000 in annual revenue. Most companies will readily provide this type of information if you sign a non-disclosure agreement—it’s your job to ask so you have full context on the business and can make reasonable asks in-line with the stage of the business.

Understand equity structures and cap tables

Most start-up jobs come with at least some sort of equity grant in the company—it’s your job to understand the equity structures and capitalization table for the business so that you understand the potential value of the equity that you’re being offered. Start-ups today may have a traditional stock option plan with a 4-year vesting period and a 1-year cliff, or they may offer incentive membership units. You may be offered restricted stock or unrestricted stock. Ask questions and learn the nuances of your equity grant. Investopedia is a great resource for understanding any concepts that may be unfamiliar to you.

Mid-level hires are notorious for not taking this step—most equity grants are very intentionally a large number of “shares,” so don’t fall into the easy trap of excitement at being offered 10,000 shares! Senior level hires always take the time to understand these nuances in painstaking detail.

There is almost always some wiggle room here too—aside from the overall number of shares included in your grant, you can always ask for provisions like a shorter vesting period or accelerated vesting if a liquidity event occurs. Changes like these often require some paperwork, but they can typically be offered if the employer is motivated to hire you.

Start-up hiring guidelines for employers

If you’re hiring people into your start-up, chances are you’re growing—congrats! Here’s how to get the right people on your team.

If you want to hire someone, it’s your job to give them what they want

If you’ve run an interview process and identified someone that you’re really excited to hire, it’s your job to get that person on the bus. If they’ve shared with you want they want, it’s your job to provide it to them or to come as close as you possibly can. It’s really that simple.

It’s much better to bring someone onboard that’s genuinely excited about the offer that you’ve made them than to pinch pennies over a small amount of money (or other benefits) that leaves them feeling less excited about their new role.

Seek to understand each candidate’s decision criteria

As a hiring manager take the time to ask each candidate about what’s most important to them in a new role. Everybody has a different financial situation, a different family situation, and different needs—proactively ask so that you can cater your offer to each candidate as much as possible.

Interview to make sure you know what skills candidates have and don’t have

When interviewing candidates to work at your start-up, you really want to understand two things.

  1. What relevant skills the person has and doesn’t have

  2. If the person is going to be a cultural fit at your company

Forget about the jumping through hoops, the strange hiring practices, and the questions designed to catch people by surprise. If they’re a cultural fit and you feel good that their skills and experience will set them up to be successful in the role, you have yourself a good hire. 

Stop looking for the magical hire

One of the biggest mistakes I see hiring managers make is looking for the elusive “magical hire.” It might be the full stack developer that’s built a handful of great digital products that you try to bring onboard for $20,000 under market salary, or the elusive marketer that’s skilled in every facet of digital marketing and has never not delivered a hockey stick growth curve.

If you continue to look for these people, you’ll inevitably come up short and will burn bridges with some really good candidates that you could have had on your team. Great job candidates can very quickly sniff out companies that are looking to find a magical hire—and in almost every instance it’s a sign that they’d be a pretty shitty employer. You can and should try to hire a great team, but remember that you’re out to find “people” not “resources.”

Run a recruiting process that makes the candidate feel wanted

Everybody wants to feel wanted—taking the time to make a candidate truly feel wanted can tip the scales in your company’s favor. It’s why we all look for love, why we all join clubs and other communities, and why we see entire cities work to recruit sporting stars to their local teams. 

I was talking to a company that knew that I was weighing a tough job decision and was going to be making a decision the next day. They made me an offer over what I asked for, I woke up to a personal email from both Co-founders, and they had other team members that I’d be working with call me the next day to tell me how excited they were about the potential of working together. Needless to say, I was super impressed. This stuff matters, shows that you care, and is easy to execute on.

Don’t oversell your company’s prospects

Another tell-tale sign of a lousy company is one where the hiring managers oversell their start-up’s potential. Sure, you want to build excitement about the opportunity to get people onboard, but do it by building credibility rather than selling a pipe dream. Be overly objective and transparent in sharing information on the market opportunity, your company’s growth rate, and potential obstacles that could impact your success. In my experience the best founders are very straightforward and almost cautious in selling the potential of their business too aggressively. 

Final Thoughts

Many of the points I’ve made in this article may come off as controversial, but I’ve followed this recipe first hand and seen it produce great results. All I’m really advocating for here is radical transparency and allowing ourselves to be human throughout the hiring process. While that may not be how you’re used to thinking about hiring, interviewing is a two way street and being completely forthcoming about what matters most to you is the seed that grows the most successful working relationships. Your start-up’s success hinges on it.

The First Six Months Of Leading Growth At A $1M SaaS Start-up

An Interview With Corey Haines, Head of Growth, Baremetrics


By Geoff Roberts 7 min read

Corey Haines is a San Diego based marketer that’s currently leading Growth at Baremetrics, a SaaS metrics and reporting start-up. He also recently launched a side project, HeyMarketers, a job board specifically for SaaS and e-commerce marketing jobs.

I caught up with Corey to discuss his first six months of leading growth at Baremetrics—and what’s to come next.

Geoff Roberts: Hey, Corey! Why don’t we kick things off by talking through what were you doing prior to Baremetrics?

Corey Haines: Sure, so when I graduated from college and it was time to line up a job, I finally landed an interview with an Amazon sellers agency. Long story short, I tried to make it clear beforehand but apparently they didn’t realize that I hadn’t actually graduated yet so two minutes into the phone interview they told me to apply again in three months and hung up on me. Frustrated, I went back to my next class and Googled “best places to work in San Diego,” and found an internship with a SaaS start-up called Cordial that hired me later that week.

The company had just raised their Series A and I was their very first marketing hire. I was super fortunate because as marketer #1 I had my hands on everything. Events, demand gen, copywriting, CRO, product marketing, email marketing, content marketing, branding… it was a crash course in literally all aspects of marketing. We continued to do really well as a company and eventually I handed off more of my responsibilities and began to specialize in the inbound marketing functions—content, webinars, email, and partnerships.

Geoff Roberts: Got it—I had a similar experience at Buildium. I think starting as a solo marketer is helpful not just in terms of exposure to all aspects of marketing, but it also forces you to learn to prioritize well. So after your time at Cordial you landed at Baremetrics in December 2018. Who is involved with growth at the company and what does the team look like (internally and agencies/partners)?

Corey Haines: As an 8-person, fully remote team we don’t really have “teams” per se as we’re one team. Everyone is involved with growth. Josh (Baremetrics’ Founder) does some marketing with his Founder Chats podcast and our blog, but also acts as a product manager in addition to his CEO duties. We have three engineers and a designer who all work on product updates, new features, integrations, and updates to our website. Erin leads customer success and has implemented a great system for us all to help handle support tickets and requests from customers. I guess it’s unconventional in some ways, but we’re a fully integrated team with a lot of overlap in responsibilities which allows us to be speedy and flexible.

Geoff Roberts: Baremetrics, ProfitWell, and ChartMogul are commonly considered the leaders in the SaaS metrics and reporting space. What do you view as Baremetrics’ strength or most important point of differentiation?

Corey Haines: As each company has matured with the market, there are some pretty clear differentiators that have developed. The first is what I’d categorize as “brand,” or essentially the culmination of the market’s perception of design, positioning, and values. Baremetrics closely aligns with the bootstrappers community with our transparency in the Open Startups movement. We share our experiences and lessons learned on our blog and are involved with other early stage SaaS founders.

The second relates to the product itself. We really excel in our ability to deliver visually inspiring metrics and deliver sophisticated data comparisons and analytics. Our software can instantly compare dates, plans, and customizable customer segments. You can also uncover trends, create goals, and add comments. We also offer two add-on features, Recover and Cancellation Insights, that give founders tools to better understand why customers cancel so that they can reduce churn and win customers back. And you can get everything at an affordable, fixed price.


Geoff Roberts: When you joined Baremetrics and assessed the situation you walked into, what’s something new that you started doing?

Corey Haines: We implemented a lot of ways to start a conversation with someone and get to know their business. I really encourage trialing users to reply to emails, allow me to send them personalized demos using their own account, and I hop on calls to consult with them about their business whenever possible. In short I encourage them to ask questions and use me as a resource.

I’ve also been much more intentional about building relationships with customers to show them how and why they should take advantage of our add-on features, Recover and Cancellation Insights. Taking a consultative and helpful approach has allowed me to get a crystal clear perspective of their business and what they’re struggling with. This allows me to give relevant advice and honestly recommend features that will help them.

There are also many new features, product enhancements, and marketing campaigns that are being born out of conversations with customers. Listening and understanding customers’ needs is a top priority and has led to a lot of new developments I’m ecstatic about.

Geoff Roberts: What’s something that you paused or stopped doing when you joined?

Corey Haines: Josh and the team were doing a great job before me and there really wasn’t anything that needed to be stopped. One thing I stopped doing early on was focusing too much on large, long-term projects. You have to have a healthy balance between what’s going to move the needle this month and provide a short feedback cycle with longer term, bigger impact initiatives.

Geoff Roberts: Finally, what was already in place that you’ve simply continued doing?

Corey Haines: Content marketing has always been Baremetrics’ bread and butter. The Founder’s Journey blog and podcast, our Academy, and Founder Chats are fantastic resources and we’d be crazy to stop investing in these areas. We’re going to continue to share our lessons and experiences, invest in organic search-focused content, and surface the stories of other founders.

Geoff Roberts: Good stuff. When you came onboard in December growth at Baremetrics had stalled a bit—the company was stuck at around $1M in ARR. What do you think caused that?

Corey Haines: Growth requires momentum and when you slow down or let off the gas a bit, it’s natural for things to stall. Putting in the work every day to spend time with trialing users and customers, invest in the community, and spin up new ways to be helpful is just as unsexy as it is effective. Growth requires intention, and we just needed someone who wakes up and goes to sleep thinking about how to grow.

Geoff Roberts: What’s been your biggest win through six months as Head of Growth?

Corey Haines: My biggest win has been the relationships built with founders and teams of amazing companies. I’m super fortunate to not only know these people, but also to be in a position to be able to help and strategize with them. I’m confident that the results we’ve seen so far will continue as long as we stay focused on serving our customers and helping the community from a place of empathy and duty.

Geoff Roberts: What’s your biggest challenge at the moment?

Corey Haines: As a team of one, there are about 1,000,001 things I could do. So the challenge is really about how to spend my time and what to spend my time on. I’ve found that scheduling my week in large blocks of time has really helped me prioritize and split my time between short-term needs and long-term vision. It will always be a challenge to feel like there’s more I could be doing if only there was more time in the day.

Geoff Roberts: Baremetrics is sitting on a lot of SaaS data—what’s one insight you can share that would be helpful to other early-stage SaaS founders with under maybe 10k or 50k in MRR?

No one, not even us, spends enough time learning from and following up with customers who cancel.
— Corey Haines, Head of Growth, Baremetrics

Corey Haines: No one, not even us, spends enough time learning from and following up with customers who cancel. Instead of figuring out how to find more customers to replace the ones that are leaving, companies should really dial in on how to minimize churn and understand why customers are canceling in the first place.

A churn rate in the double digits (e.g. 10% or above) makes growth really difficult. Instead of taking stabs in the dark about what will reduce churn and then hoping that it’ll do the trick, companies should allow customers to do the talking for them and then systematically work to improve retention based on data they can be confident in. I hate to toot our own horn here but this is the primary reason why we built Cancellation Insights.

Geoff Roberts: Call bullshit on something you see going on in the SaaS world…

Corey Haines: There are a lot of lies and deception going on with the way SaaS companies are marketing. Lying about which plan is the most popular, misrepresenting competing solutions, being intentionally unclear about the way you’re charged… it leaves a sour taste in everyone’s mouth. SaaS could use a bit more honesty and transparency.

Geoff Roberts: Cheers to that! What’s something that you’re looking forward to either personally or professionally?

Corey Haines: I can’t wait for all the product updates this year. New integrations, enhancements to existing features, and new features and products are constantly on my mind. I love our team and what we’re building.

Geoff Roberts: That’s awesome and thanks for the time, Corey. And congrats on a great first six months—Baremetrics is lucky to have you!

Outseta Company Update - June 2019

By Geoff Roberts

With the first half of 2019 coming to a close, we have some significant updates this month—if you’re an Outseta user you may have already noticed them as a large portion of Outseta just got a major facelift! Here’s what we’ve been working on.


Zapier Integration

Much of the beauty of Outseta has always been that you don’t need to integrate the core tools that your business relies on—they work together seamlessly by default. While that’s the case, Outseta is undeniably the “core” software tool for most of our customers and several have asked about a Zapier integration as a means of connecting other third party tools with Outseta.

We’re excited to share that our Zapier integration is now live and you can sign-up to get early access to it here:

CRM User Interface Redesign

We’ve also rolled out a completely redesigned user interface for our CRM, including updates to People, Account, and Deal records. Some highlights include:

  • Better filtering and sorting capabilities

  • A reorganization of the most important information on each record type

  • Better notifications of new support tickets and incoming live chat conversations

  • Customer Lifetime Revenue—Every account record will now automatically display “Customer Lifetime Revenue”—the total amount of revenue that you’ve captured from each of your customers over the duration of your relationship with them.


It is shocking to me how few SaaS companies—even established ones—have a clear sense of how much revenue each of their customers has paid them to date. This information is now clearly identified on your CRM records, making it easy to keep track of your most high value customers.

New Feature! Gmail Tracking

We now offer the ability to connect Outseta directly to your Gmail account. You can easily import Gmail contacts into Outseta and choose which contacts you’d like to track your email correspondence with in Outseta. Just navigate to CRM > Email Integration to connect your Gmail account to Outseta.


That’s all for this month—we’ll circle back with our next update toward the end of the summer!

-Geoff, Dave, Dimitris, & James

How To Nail Product Positioning So Buyers Get It, Buy It, Love It


A review of Obviously Awesome by April Dunford

By Geoff Roberts

Nothing has led me to read more business books than Co-founding Outseta. As a founder the need to “go deeper” and figure things out for yourself is very real—if you don’t do it, nobody else will!

While that’s the case, I tend to agree with the sentiment that most business books really just share an idea or two that you can take and apply to your own context and business. On top of that it seems like publishing a book is more en vogue than ever before—if you haven’t published a book yet what sort of self-professed guru are you? All of which is to say that I don’t feel compelled to write book reviews very often… but here I am doing just that!

April Dunford’s Obviously Awesome: How To Nail Product Positioning So Customers Get It, Buy It, Love It is a must read for any marketer or founder that’s struggling with product positioning. What I love about this book is that while the concept of positioning is frequently discussed in the marketing world, I agree with the author’s assessment that there’s a remarkable lack of resources out there that teach you how to actually do it. In a nutshell that’s what this book does—it’s a straightforward, no-nonsense, and highly tactical guide that any marketer or founder can use to sharpen their positioning.

Why I care about positioning (and why you should, too)

Over the past few years as we’ve been building Outseta I’ve chatted with hundreds of founders that are bringing new products to market and consulted on growth strategy with many others. In both instances the ask that I hear most often is unequivocally “we need more leads.”

In my experience, probably half of the time that I hear “we need more leads” the company actually needs to do a better job of executing lead generation campaigns. The other half of the time I find that the company really needs to revisit their “positioning”—they’re simply pushing a message on the market that’s not resonating or showcasing their product in the best light possible. When companies sharpen their positioning, all of a sudden their existing lead generation channels start delivering a lot more leads (and sales) without any increase in spending.

As a result, a significant percentage of my consulting work has actually turned into positioning work. The process that I’ve typically used has been heavily influenced by David Skok and Mike Troiano’s article Clarity of Message: Why You Need A Great Message And How To Create It and has ultimately resulted in a positioning statement, a series of key messages, a value proposition, and a few other outputs. My process has been built on a lot of trial and error—the magic of Obviously Awesome is that it provides a step-by-step blueprint to tackle positioning that anybody can easily follow.

I’ll start by sharing my own summary of the book before offering a few minor criticisms on how this book could have been even more helpful to me as an early stage SaaS founder.

My summary of Obviously Awesome

Here’s my summary of Dunford’s book—this is literally the lines of text that I highlighted as I made my way through the book. You should buy a copy yourself, but this will give you a good flavor of what you’re in for and can act as an abbreviated version for you or folks on your team.

Definition of positioning

Positioning is the act of deliberately defining how you are the best at something that a defined market cares a lot about.
— April Dunford
  • Context enables people to figure out what’s important. Positioning products is a lot like context setting in the opening of a movie.

  • Most products are exceptional only when we understand them in their best frame of reference.

How to know if you have a positioning problem

Talk to people who would be great prospects for your offering. Show them the product and explain what it does. Now ask them how they would describe what you do.

Likewise, ask existing customers about your offering and see what they say. If you see a disconnect between how your happy customers think about your product and how prospects see it, you likely have a positioning problem.

The 5 components of effective positioning

  1. Competitive alternatives—If you didn’t exist what would customers use?

    It’s important to really understand what your customers compare your solution with because that’s the yardstick they use to define “better.” Understanding what your customers see as true alternatives to your solution will lead you to your differentiators.

  2. Unique attributes—What features/capabilities do you have that alternatives do not?

  3. Value (and proof)—What value do the attributes enable for customers?

    Value is the benefit you deliver to customers because of your unique attributes. If unique attributes are your secret sauce, then value is the reason why someone might care about your secret sauce.

  4. Target market characteristics—Who cares a lot about the value? Try to identify the

    characteristics of a group of buyers that lead them to really care a lot about the value you deliver. Your sales and marketing efforts need to be focused on the customers who are most likely to buy from you. Your positioning needs to clearly identify who these people are.

  5. Market category—What context makes your value obvious for your target customers? This is the

    market you describe yourself as being a part of to help customers understand your value. Market categories serve as convenient shorthand that customers use to group similar products together.

Because these relationships flow from one to another, the order in which you define the components is very important (follow the order in which they are presented above).

The step-by-step positioning process

Follow this process to define your product’s positioning.

  1. Understand the customers who love your product

    Your best fit customers hold the key to understanding what your product really is—look at ecstatic customers and their opinions vs. your overall customer base. Make a short list of your best customers—if you don’t have super happy customers already, hold off on tightening up your positioning. Until you have more experience with real customers, it’s better to keep our minds open and our positioning loose, and see what happens.

  2. Form a positioning team (3-12 people)

  3. Let go of positioning baggage

    Get agreement from your team that although the product was created with a certain market and audience in mind, it may no longer be best positioned that way.

  4. List your true competitive alternatives

    The features of our product and the value they provide are only unique, interesting, and valuable when a customer perceives them in relation to alternatives. Start by asking customers what problems they are trying to solve. Understand what a customer might replace you with in order to understand how they might categorize your solution. Teams usually end up with 2-5 groups of alternatives.

  5. Isolate your unique attributes and features

    Strong positioning is centered on what a product does best. Once you have a list of competitive alternatives, the next step is to isolate what makes you unique or better than those alternatives. In this step stay focused on features and capabilities (attributes), rather than the value those features drive for customers. List all the capabilities that you have that the alternatives do not.

  6. Map the attributes to value themes

    Features enable benefits, which can be translated into value in unique customer terms. Cluster the value into themes—look for patterns and shorten your list to 1-4 value clusters.

  7. Determine who cares a lot

    Once you have a good understanding of the value that your product delivers versus other alternatives, you can look at which customers really care a lot about that value. An actionable segmentation captures a list of a person’s or company’s easily identifiable characteristics that make them really care about what you do.

  8. Find a market frame of reference that puts your strengths at the front and center and determine how to position in it.

    Make your value obvious to the segments who care most about that value. We position our product in a market to trigger a set of assumptions—about competitors, features, and pricing—that work to our advantage.

There are 3 types of positioning as you consider how to position in a given market

  1. Head to head (to win a market)—You aren’t claiming to be better for a certain type of customer; you’re claiming to be better for most if not all customers. Only do this with a new product if a market leader has not been established. The advantage is you don’t need to convince people that the category needs to exist.

  2. Big fish, small pond: positioning to win a subsegment of an existing market—You get the advantage of a well defined category without the stiff competition. Your focus is showing there’s a subsegment of the overall category with a specific set of needs that the current category leaders are not addressing. The subsegment needs to be easily identifiable—meaning if you had to create a list of prospective buyers, you could figure out a way to do that. First educate the targeted subsegment about how a general purpose solution is not meeting their needs.

  3. Create a new game: Positioning to win a market you create—Sometimes a market can be created by combining one or more existing markets to form one with different buying criteria. Only use this when you have evaluated every other possible existing market category and concluded that you cannot position your offering there, because doing so would fail to put the focus on your true differentiators and value. To credibly create a new category, you need a product that is demonstrably, inarguably new and different from what exists in other market categories. Category creation is about selling the market on the problem first, rather than on your solution.

“The most successful efforts in category creation do not result from company executives creating an acronym at an off-site. Rather they are discovered from deeply understanding a subset of customers.”
— Mark Organ, Founder of Eloqua

Positioning Canvas

This is simply a document or set of questions that you should complete as you begin the work of figuring out your positioning.

Positioning Canvas FINAL.png

Putting positioning into play

Once you finalize your positioning, putting your positioning into play typically starts with developing your sales story.

  1. Starts with the definition of a problem your solution was designed to solve

  2. Introduces what the “perfect world” would look like

  3. Introduces the product or company and positions it in a relevant market category

  4. Flows into the value themes and a bit more detail about how the solution enables that value

Where Obviously Awesome could be even awesom-er

Ultimately I loved this book and found it extremely useful. However, there’s two specific instances where I felt like this book left me hanging a bit.

Positioning for an early stage start-up

Dunford writes, “If you’re a start-up and don’t have super happy customers already, hold off on tightening up your positioning. Until you have more experience with real customers, it’s better to keep our minds open and our positioning loose, and see what happens.”

I understand this sentiment—it reminds me Alex Turnbull’s article Attention Start-ups: Stop Selling To Start-ups where he makes the point that companies should widen their net rather than focusing at an early stage on the markets that are most familiar to them. Keep your positioning loose and your targeting wide and you might be surprised to find who is actually getting the most value out of your product.

While I appreciate that you don’t yet know who your best customers might be, I find that this advice isn’t terribly helpful. You need to think about positioning to some extent even as an early stage start-up, and I can’t imagine that loose positioning—we offer a product that’s CRMish—could possibly be helpful.

My own take is that you need to start with an educated guess with regards to your unique attributes, who cares about them most, and the market category you think you can most effectively position your product in. From there you should plan on running experiments to test the effectiveness of your positioning, moving rapidly to test new positioning if it doesn’t seem to resonate. In other words, systematically test new and different positioning until you find a position that seems to resonate rather than over-generalizing your product.

Positioning a platform solution

I didn’t read this book under the context that we have a positioning problem at Outseta—if anything, I’ve gotten feedback that prospects “get it” pretty quickly when looking at our website. What I have heard is that most prospects either consider us a “CRM” or look at us as an “Authentication and subscription management solution.” I think both categorizations make sense, but all things considered our positioning has been best articulated by this image.

This image has articulated Outseta’s positioning better than anything else to date.

This image has articulated Outseta’s positioning better than anything else to date.

Obviously Awesome is an incredible resource if you’re marketing a CRM, or an email marketing tool, or blueberry muffins. But when I turned this book towards our own business it wasn’t particularly helpful in helping me think about Outseta’s positioning—as all all-in-one platform solution, I was still left scratching my head a bit. Let’s talk through that.

First, I need to decide on how to position in a given market. Again the choices are:

  1. Head to head (try to win a market)

  2. Big fish, small pond (try to win a subsegment of an existing market)

  3. Create a new category

Given that Outseta plays in a number of very mature and competitive markets—CRM, subscription billing, customer messaging, and help desk—I can easily rule out head to head positioning. We’re not going to win outright if we take on Salesforce. Or Intercom. You get the idea.

I initially thought about creating a new category—there really isn’t another product out there that offers the scope of capabilities that Outseta does to early stage SaaS businesses. But while our platform is unique in that sense, each of our key capabilities is already well understood as CRM, or email marketing, or subscription management, for example. Slapping a new label on these features in the vain of “creating a category” just doesn’t feel authentic to me.

That leaves us with big fish, small pond positioning—I can get behind that. We need to choose a market or category and fight for the subsegment of customers at the lower end of that market that’s typically defined as makers, indie hackers, or bootstrapped SaaS companies. Game plan!

But choosing the market category—and all the assumptions regarding features, pricing, and competitive offerings that comes with it—proves to be really challenging. Are we primarily a CRM? A subscription management platform? A customer messaging platform? A help desk?

The reality for us is that we offer the basic features and capabilities expected of software products in three or four preexisting and well understood software categories. In a lot of ways I don’t think it makes much of sense for us to have to choose to align ourselves with just a single one of these categories.

The fact of the matter is whichever of those existing markets we choose, our product is not going to be the most compelling when evaluated against the criteria that products in that chosen market are measured against. Outseta’s value comes from the breadth of the features we offer across the different categories of software that all early stage SaaS businesses need.

If we have to align ourselves with a pre-existing category, I’d choose either “CRM” or “subscription management.” But those markets themselves are pretty different—are we competing with Hubspot CRM, Pipedrive, and Copper or are we competing with Chargebee, Recurly, and Chargify? That’s a big decision with lots of trickle down consequences.

My gut tells me that at our core we’re primarily a subscription management platform, because our customers find us early on to help them manage subscriptions—the contact management and CRM aspects of the product come into play at a later stage. The alternative solution we hear a lot about at an early stage is companies building their own subscription management logic and other required scaffolding on top of Stripe.

But beyond just subscription “management,” I think our positioning likely needs to be something closer to a subscription “growth” platform. We’re not just managing subscriptions, but actively providing a series of tools to help you grow and support your subscriber base that the other subscription management platforms simply don’t offer. I’m not sold on that yet, but it’s the way I’m leaning.

These challenges or criticisms are fairly unique to our context and product, but in the vain leaving a balanced review they were the shortcomings of Obviously Awesome for me specifically. April Dunford’s book is gem—if you’re working on your positioning, it’s the best place yet that I’ve found to start.

Should My SaaS Start-up Launch A Podcast?


By Geoff Roberts

One of the questions I field most often from other start-up founders and companies I help with content strategy is, “Should I start a podcast?” Podcasting is undeniably hot at the moment, especially with younger consumers—according to the New York Times 40% of people between 12 and 24 years old listened to a podcast last month, up 10% from 2018. Droves of people and companies are launching podcasts, but just as with any new marketing channel many of them are simply following the trend rather than thinking critically about whether a podcast makes sense for their business.

My objective with this post is to provide some practical advice on whether a podcast is right for your business. I’ll share why we’ve decided not to start one, and will assess the relative opportunity podcasts, blogs, and video content offer to SaaS start-ups.

The benefits of podcasting

Podcasting comes with many benefits, aside from the simple fact that more listeners are tuning into podcasts every day. Here are a few of the most significant.

Podcasts are easy(er) to produce

Generally speaking, podcasts are easier to produce than video or written content. I know that this comment will draw ire from some folks, and I’m the first to agree that writing, podcasting, and producing video content all come with their own unique challenges and requisite skills that must be developed to do them well. I’m certainly not in the camp of, “podcasts are just two people talking to each other for 20 minutes.” That’s a naive perspective that’s disrespectful to the people who have worked hard at perfecting the craft of podcasting and growing their audiences.

While that’s the case, I do believe that podcasts are generally easier to produce than written or video content. Video is without question the most difficult, as the actual substance of the content, the audio, and the visual elements all must work together in harmony. But I believe truly writing well is more difficult, too—for most of us “writing” is a process reserved for bad memories of drafting essays in some long ago forgotten English class. I know many more people who can carry great conversation but can’t write to save their lives than vice versa.   

Also, consider the relative time involved in creating a podcast episode versus written or video content. Some points of reference:

  1. Noah Kagan’s podcasts typically last 45 minutes to an hour—he says each episode takes 8-10 hours to produce.

  2. Nathan Latka’s Top Entrepreneurs podcast features short, 15-20 minutes episodes. He books two six-hour long recording sessions each month where he records the content for 30 new episodes, and has outsourced the rest of his process (including editing, which he pays about $1 per minute for).

  3. Paul Stephenson’s SaaS Marketing Insights podcast features 20 minute episodes that take about four hours each to produce.

  4. Justin Jackson and John Buda’s Build Your SaaS podcast features episodes of 45 minutes to an hour—Justin estimates each episode takes just over two hours to produce.

For sake of comparison, many of the blog posts that I’ve written for Outseta focus on our own company and entrepreneurial journey. Because I’m writing on a topic I know well, where I’m the expert, it’s routine that I’ll spend 4-6 hours in total on these posts. But when I’m writing similar length content (2,500-4,000 words that takes 15-20 minutes to read) that requires interviews, research, and several rounds of revisions it often takes me 12-18 hours to create a great post.  

"In my experience as a writer I can either write a story that leverages my existing skills or expertise in a couple hours or I can write a story that requires new research and interviews that can take anywhere from 10-40 hours,” agrees Michael Thomas, Founder of content marketing agency Campfire Labs.

Video content—assuming you’re not making selfie-style Linkedin videos—typically takes even longer to produce.  

Podcasts can be consumed while multi-tasking

Podcasts can be consumed while performing other activities in a way that video or written content can’t—for example, you can listen to a podcast at the gym, while cooking dinner, or while driving. I think many people glaze over this benefit far too quickly.

That’s too bad, because in my eyes this is the single greatest benefit of podcasting! As marketers we are all competing for the attention of our audiences and there’s a limited amount of our audience’s mental real estate that we can occupy. Everybody has time throughout their day whether it’s in the car, at the gym, or while you’re simply walking down the street where you can listen to a podcast but you can’t watch a video or read written content. That’s a very real marketing opportunity—there’s a bigger lot of time that you can potentially occupy, as well as less competition for a listener’s mental real estate. Go fill it!

Podcasts are more personal

The auditory nature of podcasts ensures that personalities, point of emphasis, sarcasm, and other nuances of language aren’t lost in translation. We’ve all read a text message and misinterpreted it without the benefit of these important contextual triggers, so this is significant in communicating your message and points well. Hearing someone’s distinct voice and tone makes podcasts more personal than written content, which helps brands build a more authentic connection with their audience.

Podcasts are very guest friendly

Having been a guest on several podcasts now, I can say that being a podcast guest is pretty great—it’s quick, efficient, conversational, and typically less involved than co-authoring a blog post or producing a video with somebody. When someone asks you to be a guest on their podcast, it’s very easy to say yes.

When you’re on the other side of the table and you’re the one recruiting podcasts guests the ask is simple and straightforward—show up and have a conversation with me for 30 minutes or an hour. The conversation is the product—it will need some editing and production polish, but it tends to be closer to the finished product than you’d be if your were writing a blog post or producing a video.

Podcasts are an easy way to produce long form content

Podcasts are a fast, direct path to creating the long form content that search engines love. While I don’t profess to be an expert on the extent to which podcast content helps with SEO, I do know that Google wants podcast content to be searchable. If there’s a north star that’s served me well when it comes to SEO, it’s that Google’s intention is to surface the best and most relevant content in response to any given search query—of course that content could be delivered in the form of a podcast (or a podcast transcription).

If there’s a north star that’s served me well when it comes to SEO, it’s that Google’s intention is to surface the best and most relevant content in response to any given search query—of course that content could be delivered in the form of a podcast (or a podcast transcription).

A 15-minute podcast transcription tends to be about 2,000 words—try writing a 2,000 word blog post 15 minutes. Podcasting is a much more efficient path to generating long form content for search engines to crawl.  

How do I decide which form of content to invest in?

Now that we’ve covered the benefits of podcasting, the question for start-up founders remains; which form of content should you be investing in? For bigger, less resource constrained companies the answer is often “all of them” and that’s totally appropriate; serving up content in a variety of formats likely makes sense. But for more resource constrained SaaS start-ups, this can be an important strategic decision.

My leading piece of advice is to follow the skills that you have on your team—if you have a savvy writer on your team, write blog posts. If someone on your team is a great conversationalist or interviewer, launch a podcast.

When it comes to the content we’ve produced so far at Outseta, I’ve primarily chosen to invest time and effort into generating long form blog content. While I can film a Soapbox or Loom video, I’m definitely not a videographer. And while I have a lot of experience conducting interviews, I’m much more effective taking the rough output of those conversations and weaving it into a compelling narrative than I am leading an interviewee intentionally and smoothly through a conversation. I’m no Bob Costas, so written content has won out for us.

Aside from the skills on your team and the content consumption tendencies of your audience, you also need to consider your product and the market that you’re trying to reach. For example, if your company serves the travel industry listening to a podcast that speaks about “the cool blue crystalline waters of Bora Bora” probably isn’t going to be as compelling as watching video content showing those waters gently lapping up on the island’s shores. This sort of market probably lends itself to more visually oriented video content, just as a company building word processing software might lean more towards written content.

Why blogging will make a comeback

I’m personally betting that blogging will have a resurgence of sorts, as the market for both podcasts and video content continues to expand. Why? Because whether we’re talking lead capture forms, or blogs, or bell-bottom jeans these things are largely cyclical—especially in the world of B2B SaaS.

As more content producers focus on channels aside from blogging, I also see the number of capable writers dwindling. We’re living in a time where written communication is increasingly taking the form of emojis and shorthand, where technology bootcamps are generally more interesting to students than English classes. Google’s smart reply feature is even trying to write our email responses for us.

While consumption patterns are undeniably growing faster for video and podcast content, movement in that direction will result in an even shorter supply of writing talent—providing an opportunity for companies that choose to invest in superlative written content.   

Why video content is King

Writing and podcasting aside, it’s very clear to me that video content will eventually reign supreme. I thinks this is the case for two reasons:

  1. The barrier to entry with video content is the highest. It’s simply more difficult to put together well produced video content than written or audio content.

  2. Video is as engaging, vivid, and rich of a format as content can take. For these reasons it can more effectively build brand authenticity, appeal to the emotions of buyers, and move an audience to action.

Because the barrier to creating video content is highest, there’s less of it out there. Type almost any search query into Google, then specifically search Google Videos for the same search terms. The difference in the quality, number, and relevance of the responses is significant. This is why SEO experts like Neil Patel have chosen to go all-in on video content recently—there’s simply more real estate and top search positions easily up for grabs with video.

There’s no simple answer to whether your company should be investing in video, written, or podcast content—but if you understand the unique benefits of each format, your target market, and your team’s internal skill set you can deliberately build your audience by investing in the content format that makes the most sense for your company.

Outseta Company Update - May 2019


Our approach to pricing experimentation

By Geoff Roberts

When we began working on Outseta our product vision was fairly straightforward—bring together the core software tools that all early stage SaaS start-ups need. We deliberately set out to build tools to serve the lower end of this market, intercepting companies shortly after they’re founded and scaling with them until they reach about $5M in annual recurring revenue (ARR).

While our vision for the product has always been clear, one thing we realized early on was that pricing Outseta was going to be particularly challenging. On one hand we saw a clear opportunity that we could attack—most of our venture-backed competitors offer some sort of “start-up plan,” but their products become expensive really quickly once you graduate from that first pricing tier. On the other hand, by serving bootstrapped SaaS founders we’re selling to a price conscious audience and opening ourselves up to competition from freemium products.


But perhaps our biggest challenge has been finding the right pricing structure given the breadth of our product:

  • Most CRM and help desk tools offer seat based (per user) pricing

  • Most email marketing tools charge based off of subscribers

  • Most billing systems charge a percentage of revenue processed

Given that we offer all of this functionality, what value metric should we hinge our pricing too? And how can we implement pricing that’s both fair and easy to understand for our customers?

If we’ve learned anything about our pricing so far, it’s that we haven’t quite gotten it right yet—this post details for our prospects, customers, and anyone else interested in pricing SaaS products what we’re going to do about it.

Why I’ve always leaned towards “charge more”

A couple of weeks ago I attended MicroConf for the first time, a conference filled with self-funded software entrepreneurs that match Outseta’s ideal customer profile. My objective at the conference was clear—get as much feedback on Outseta’s pricing as possible. If there was a mantra coming out of the entire event it was “charge more,” a message perpetrated largely by Patrick Mckenzie of Stripe. Then just last week Justin Jackson published an article entitled Should We Always Charge More, noting the benefits of lower pricing that gives your customers value above and beyond the price they are paying for your products.

I tend to lean more towards the “charge more” camp based on my past experiences. When I was head of marketing at Buildium, we entered the market with a product that started at $20 per month. Soon a new incumbent and Buildium’s biggest competitor, Appfolio, entered the market with a price point starting at $200 per month. The products were nearly identical in terms of functionality.

Our pricing was deliberately defensive and it was really effective in helping Buildium capture market share—we signed up over 10,000+ new customers over 5 years—far more than Appfolio. But we found that many prospects immediately assumed Appfolio was a better product because of their price point, which led to many larger companies choosing Appfolio over Buildium. Both companies have gone on to do very well, but in retrospect a lot of the bigger companies Buildium would have loved to serve in later years had already signed on with Appfolio.

When I left Buildium, I made a short list of the most important lessons that I’d learned over the previous five years. Included on that list was, “If you have the opportunity to do something similar again, start off with a higher price point like Appfolio did.” Not only do you reap the benefits of being perceived as a better product simply on the basis of price, but it also allows you have equivalent revenue with fewer customers to support. And your customers will be subjected to pricing increases less frequently as you work to monetize your customer base.

As Justin Jackson’s article points out, most pricing advice (like “charge more”) is fairly generic and lacks context on both the stage of your company and the market you’re serving. While I have a bias towards “charge more,” competing in a market with so many freemium offerings and where our customers may not yet be generating revenue dictates that we have a price point that’s very accessible. Our pricing to date has tried to serve both objectives.

Outseta’s original pricing

Outseta’s original pricing

The “Founder’s Plan” eliminates any barrier to entry for our product, giving start-ups access to all of our features and as much time as they need to adopt the platform. They can setup their pricing plans, track their sales pipeline, receive support tickets, send emails, and invite as many team members as they like without incurring any charges.

Once a user has over 250 contacts and starts using the product in earnest, they’ll move up to our $99 per month “Start-up Plan.” This plan is designed to be a fantastic deal opposed to the alternative of buying a handful of point solutions, while still charging a healthy rate that we believe is fair given the value we’re providing.

We added the $249 “Growth Plan” after hearing from a prospect whose company was at $1M in ARR that our existing pricing was “too start-uppy” and left him with the impression that we couldn’t serve his company’s needs—an impression that he said was not at all correct once he took a look at our product.

What we learned about Outseta’s pricing

Over the course of 2018, my conviction grew that we didn’t quite have our pricing right—over the past few months I set out to capture as much feedback on our pricing as I could. I created the document below that outlines our existing pricing, the feedback we’ve received, and some pricing experiments that we’re considering running.

Outseta Pricing Experiments (April 2019)

I then shared this document with the following groups and asked for their feedback.

  • MicroConf attendees

  • Justin Jackson’s “Mega Maker” group—a private, pay-to-play Slack community with a lot of bootstrapped SaaS founders

  • Existing Outseta customers

  • Prospects that are on our free “Founder’s Plan” that have been consistently using our product

The feedback we’ve received has been wide ranging, and interestingly enough several people have shunned pricing models that would actually result in them paying us less money. Here’s a smattering of the feedback we’ve received.

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After gathering all of the feedback that we could, no obvious answer emerged. Some people thought contact based pricing was a no-brainer, while others thought contacts had no real correlation to growth. Most people ignored the notion of user based (per seat) pricing, despite the fact that it’s the norm for CRM and help desk products and in most cases would have been the cheapest alternative. But out of all the feedback we received two themes surfaced most consistently:

  1. Going from a freemium plan to a $99 per month plan is too big of a jump—it causes some sticker shock. We need to make our entry level paid plans more accessible.

  2. Our customers want the price they pay us to scale in tandem with their own revenue growth.

We’ve since designed two pricing experiments designed to address this feedback.

Outseta’s upcoming pricing experiments

Going back to our product vision, one of the problems we set out to solve when designing our own billing system is exactly what we’re living through right now—most SaaS start-up’s really have no idea what their pricing should be when they’re just starting out. Our “Start-up Plan” pricing was loosely based on looking at the price of alternative solutions to Outseta, but for the most part the $99 per month price tag was pulled out of thin air. What start-ups really need is the ability to iterate on pricing quickly to figure out what works and what doesn’t.

Outseta competes price wise against a tech stack that integrates point solutions like these

Outseta competes price wise against a tech stack that integrates point solutions like these

With this in mind we designed a subscription management and billing system that supports the billing scenarios and pricing models most commonly seen in start-up SaaS companies:

  • Manual invoicing

  • Monthly and annual subscription payments

  • Metered (usage based) pricing

  • Unit based (per user, per seat) pricing

  • Freemium and free trial models

  • Requiring credit card information upfront or at free trial expiration

We also built a javascript pricing widget that can be dropped into your website’s pricing page, allowing you to change pricing plans and models from within Outseta with your website and registration workflow updating automatically to your new plans. This allows for rapid experimentation with new pricing plans and models—what this means for us in practice is we can deploy the tests outlined below in minutes.


Based on the feedback we received, I seriously wrestled with the notion of offering a “pay what you want” plan allowing customers to name their own monthly price as long as they provided us with feedback on why they chose the price that they did. I think this would have been a great way to capture further feedback on our pricing, it would consider every customer’s unique financial situation, and it would also give us an opportunity to create a bit of a PR splash.

While that’s the case, I ultimately decided against this option—other companies have tried this before with mostly lackluster results, and I think it could send the wrong message about our product and erode our credibility. Instead, we’re going to be running two 60-day pricing experiments.

May-June 2019 Pricing (Experiment #1)

Throughout May and June we’re going to launch “Experiment #1”—contact based pricing with smaller tiers. We’ve maintained a freemium tier with a smaller contact limit to give start-ups as much time as they need to implement Outseta, but the paid version of Outseta will be much more accessible—$29 as opposed to $99. Companies can continue to invite as many team members as they want. This pricing is now live on our website.

Outseta’s pricing May-June 2019

Outseta’s pricing May-June 2019

These plans were designed to alleviate the sticker shock some prospects mentioned when our entry level paid pricing plan was $99 per month. That plan also provided a much greater volume of contacts than most customers actually needed, so the smaller pricing tiers help to ensure that customers are only paying for the number of contacts that they actually need.

Beyond 5,000 contacts we’ll eventually add a pricing calculator on our website where prospects can enter their number of contacts to get a pricing quote.

I think this experiment solves most of the issues we’ve outlined, but I still have two points of hesitation.

  1. “Contacts” isn’t always understood by prospects.

  2. Pricing based off of contacts may deter some companies importing all of their contacts during onboarding (an action we want them to take).

July-August 2019 Pricing (Experiment #2)

Throughout July and August we’re going to launch “Experiment #2”—user based pricing that allows companies to add as many contacts as they like without moving through pricing tiers. This pricing is extraordinarily simple and mimics what most other CRM and help desk tools are doing, while again helping to alleviate the sticker shock of the $99 per month price point.

  • $19 per user per month

For a single founder or two co-founders, Outseta will represent an amazing deal at $19 or $38 per month, and once a company has 5-6 employees using the software they’ll have grown to our original $99 per month price point.

This pricing model is the norm for the industry, so I think it’s worth testing. But this also opens us up to some vulnerabilities most CRM products don’t face—if we allow unlimited contacts, we’ll need to put a cap on email usage because we incur costs when emails are sent. Most CRM products don’t have to worry about this because they don’t also offer email marketing.

Subscription billing update

In addition to making our paid plans more accessible, we also wanted to better align what are customers are paying us with the revenue they’re generating. To date we haven’t made any money on payment processing—we’ve instead simply covered Stripe’s 2.9% payment processing fee.

Going forward we’re going to charge a 1% payment processing fee in addition to Stripe’s 2.9%. Payments processed by our other payment processing partner, Forte Payment Systems, will continue to be charged at a flat rate of 2.9% per transaction.

We’re also excited to announce that Outseta recently became part of Stripe’s Verified Partner Program. You can learn more about Stripe and Outseta here:


How we’ll handle existing users and customers

A hallmark of our pricing strategy will always be honoring and celebrating our existing users and customers—what that means in practice is that while these experiments are running, our existing users and customers will be given the option of staying on our original pricing plans or changing to either of the new pricing structures that we’re experimenting with. That gives them options, flexibility, and we think it’s the right thing to do.

For new users considering Outseta for the first time, we’re publicizing these experiments ahead of time and you’ll be subject to the pricing that’s advertised on our website as we go through the process of running these experiments.

This process is imperfect, but we’re excited to see which pricing plan and model drives the most conversions. We asked for a lot of feedback, but we’re excited to now let the data do the talking.

-Dave, Dimitris, Geoff, & James

The Hiring Opportunity Most B2B SaaS Companies Are Missing

Why most SaaS companies are blind to some of the best talent on the market

By Geoff Roberts 9 min read

I believe that most SaaS companies are missing out of a major opportunity when hiring—the opportunity to hire more part-time help, where the employee acts as a fully integrated (albeit part-time) member of the team on an ongoing basis. I think that this is likely true in most industries, but it’s particularly true in SaaS where there’s a rapidly growing population of extremely talented people—call them bootstrapping co-founders, indie hackers, makers, etc—that are working on their own side projects.


This group tends to be talented, extremely driven, and more often that not is looking for ongoing work with a company that can provide more stability and income than their side project does. Ignore them at your own peril.

I think this will be one of the next major hiring trends that you see in the world of SaaS start-ups. Just as hiring remote employees has opened the door for smart companies to dramatically open up the talent pool they can pull from, I think hiring managers will soon come around to the notion that not every employee needs to be hired in a full-time capacity. In fact, there are huge benefits to hiring folks that aren’t full-time that I think most employers never stop to fully consider.

Let me be very clear—this is not an argument for consulting or the so-called gig economy and I’m not arguing against the need for full-time employees—if you’re hiring a COO, for example, you’re probably going to need that person full-time. This is an argument for being more open to hiring part-time employees that work with your company on an ongoing basis. For the sake of this discussion let’s consider that employees who work with your company 2-3 days per week.

My own part-time path

I want to start by clarifying my situation up front—for the past two years I’ve been splitting my time between working on my own start-up, Outseta, and working with another SaaS company in an ongoing, part-time capacity. We’re bootstrapping Outseta and are deliberately taking a long-term, organic approach to growth—it will likely be another year or two before Outseta can support a full-time salary for myself and the rest of our team. Until that day comes I’ll continue to work with another business; it’s something that I need to do to cover my living expenses, but it’s also been hugely beneficial to me.

I’m not writing this post with my own self interest in mind—I’m writing it because I just returned from MicroConf, an event attended by hundreds of other entrepreneurs who are working on their own start-up projects, most of them in a part-time capacity. Most of the people that I met at the event were super talented, exceptionally driven, and would jump at the opportunity to work with a great company in a part-time, ongoing capacity.

This group would benefit from greater stability and consistent income—a situation far preferable to consistently looking for project-based consulting work. And employers benefit from bring top-tier talent onto their teams, while building a long-term working relationship that allows the employee to maximize their impact. I know this not only from my own experience but from talking to countless other folks last week who expressed this sentiment, and best of all there’s a lot of these people out there. If you’re not open to hiring them, I think you’re missing out. Let’s dig into the reasons why.

A small team of “A” players outperforms a larger group of “B” players

Most of us agree that we can accomplish more with small, superlative teams than we would with larger, less remarkable groups. I’d follow that up by saying that someone that’s a top-level talent will most often make a bigger impact on your company in 2-3 days per week than a less talented colleague would in a full-time role.

Think of the best CTO-level software developers that you know—do you think your product would progress faster if they were building it 2-3 days per week, or if you hired an average developer in a full-time capacity? Consider how much time is typically wasted or unproductive for any employee working in a full-time role—time spent checking social media, chatting at the proverbial water cooler, etc. I’d err on the side of working with the better developer every time, and I think this holds true across most job functions.

I’ve seen this play out firsthand in the context of my own start-up, where the first employee that we added outside of our founding team was James Lavine, who leads design for Outseta. James is an experienced designer who is helping us in a very part-time capacity—20 hours per month—but on an ongoing basis. He’s been able to build our brand and product design from the ground up, chipping away at our most important design work with the benefit of ongoing context and immersion into what’s happening with our business. Because of his experience and expertise James delivers good work that requires minimal revisions the first time around, and I know the output we get from James in just a few hours per week beats what we’d get if we hired a junior designer into a full-time role.

You don’t need more people or more hours, you need fewer hours from better people.

Tap into a greater diversity of experience and expand your network

Perhaps the most unsung benefit of this approach is that by working with people who are also working on other projects, you get the benefit of their other experiences and their networks.

For example, maybe your company sells its products primarily online using a low-touch customer acquisition model. If someone on your sales or marketing team is also working with another company that has a much slower moving, high-touch sales cycle, then that experience may come to directly benefit your company if you eventually move up-market to sell bigger deals. Or maybe it’s as simple as you’re getting ready to experiment with Facebook Ads and the marketer that’s helping you in a part-time capacity has already been running Facebook Ads for another business. Those experiences are very real benefits to your company.

Additionally, by working on more than one project on an ongoing basis part-time employees are part of multiple teams. They get to know more people, make more connections, and work with different agencies and partners. They’ll have opinions, resources, and people that can help your company that employees who are more insulated by being a full-time employee at your company can’t bring to the table.

Think of your own past jobs and the relationships you’ve built at each—you likely lean on the network that you’ve built whenever you need it in your current job, right? When people have a greater diversity of experiences, their networks (and subsequently your company’s) grow faster.

You get access to better talent for your money

Your money also goes further when hiring part-time employees—an MIT study found that benefits and other related costs often cost employers an additional 25%-40% of a full-time employee’s salary. So if you’re paying someone $100,000 per year, your actual costs are likely $125,000-$140,000 annually. Most companies that hire part-time help bring on part-time hires as 1099 contractors, saving these expenses.

Consider the alternative of hiring a Junior Software Developer at a salary of $80,000 per year. Add 40% for benefits and other costs, and that person is costing your company $112,000 per year. What if instead you can hire that CTO that you’ve always admired, who has a track record of success with several previous ventures. The person would typically command a $200,000 annual salary, but you can work with them 2-3 days per week for $100,000 per year.

Who do you want on your roster, the experienced CTO with a track record of success (and the $12,000 in savings you just bagged to invest elsewhere) or the junior dev?

People working on their own projects tend to be ambitious people well-suited to start-ups

We should also be attracted to employees looking for part-time, ongoing roles specifically because many of them are working on projects or start-up ideas of their own. If your company is a start-up itself, it will likely flourish when it’s filled with other entrepreneurial people who are less risk averse and are comfortable working without much structure and heavy doses of ambiguity.

When I look to hire for almost any role in a start-up (and particularly marketing roles) the number one thing I look to assess is the ambition and fire in the belly of the candidate. People who are working on their own start-up ideas tend to have more than ample doses of both.

We’ve misunderstood what people want from the gig economy

Finally, I think this hiring strategy represents a very real opportunity for hiring managers because I think we’ve fundamentally misunderstood what people want—and what’s led to the creation of—the so-called gig economy.

People generally don’t want to be freelancers for the sake of being a freelancer. Maybe they’re hoping to build their experience, maybe they’re working on their own start-up and need some additional income, or maybe they place great value on their ability to work remotely and have a flexible schedule. Whatever their reason may be, talk to anyone who does freelance work and the last thing they typically want is a series of short-term contracts that require them to be consistently spending time looking for new work. There’s a huge opportunity cost there—time spent searching for work rather than making money.

The final problem with the gig-model is while consultants or people working on short-term contracts can provide a new opinion or perspective, they typically don’t have the time to work with the company long enough to get to know the market and the nuances of the business, to build relationships, or to optimize performance on an ongoing basis based on past learnings.

Building long-term relationships with part-time employees allows you to realize these benefits, and it’s actually what the employee is looking for, too. They reap the benefits of greater stability and can afford to spend more time helping your company at a more competitive rate because they don’t have to factor in time looking for new work when setting their fees. Typically they can also make a bigger impact on your business when they have the context and ability to implement long-term strategies that can only come with a longer-term working relationship.


Not everyone needs to run out and hire experienced, part-time help—there will always be roles that require full-time hires, just as there are roles and industries much better suited to co-located rather than remote teams.

But start-ups themselves are based on the notion of doing more with less, and I think better talent can accomplish more in fewer hours. With the market for top-level talent as competitive as it is in the world of B2B SaaS, I’m surprised that more companies don’t see the allure of this approach as an alternative to seriously consider.

The market of top tier-talent that’s looking for part-time, ongoing work is very real if you’d open your mind (and company) to it.

Free Trial or Freemium? Going From 0 to 100,000 Users In Six Months With Wes Bush


Wes Bush is a SaaS marketer who has quickly developed a reputation as “the free trial vs. freemium guy.” He helps SaaS leaders launch and optimize free trial and freemium models via his consultancy, Traffic is Currency, and is also the founder of the Product-Led Summit.

I caught up with Wes to talk about his free trial vs. freemium framework, our own customer acquisition process, and the start-up scene in Waterloo, Canada.

Geoff Roberts: All right, so first thing's first—before just a moment ago we’d never met, but I have come to know you in online circles as the free trial vs. freemium guy. Tell me about your early career path and how you decided to zoom in and focus on this one particular problem.

Wes Bush: I feel like I really stumbled into this space and I've been doing marketing and demand generation for the last seven years now. I’ve tried virtually everything when it comes to generating demand and leads for a business. But it wasn't until I launched a freemium product and we went from 0 to 100,000 users in six months, where I was just absolutely amazed by the fact that that was possible. We were delivering so much value and I really came to see freemium and free trial models as a supercharged lead magnet for a business. You can make that lead magnet also turn into customers for your business. So once I realized that I just saw that this is the future.

People want to try before they buy and even if you look at a business like Costco, you want to get a sample of something to test it out and see if you really like it. Or you're thinking of buying an expensive cologne or a perfume, you want to try it before you actually buy it because you might hate it and never want to wear it again. So it's a really great way to build trust as well as find out if the solution is right for you or not.

Geoff Roberts: Good analogies. What was the business that you mentioned that went from 0 to 100,000 users in six months and what were you doing previous to offering a freemium model at that company?

Wes Bush: That was at Vidyard and we did have a free trial at the time but it wasn't the most successful. A lot of free trials for B2B SaaS products, when you sign up there really isn't too much value right away unless you connect your data or maybe you upload something and in Vidyard this was the case. You wouldn't be able to see value quickly because you didn't have any videos and unless you signed up for the free trial with the expectation that you’d upload a video right away, you weren’t going to see value. So we built a freemium product to help people create videos very quickly—it would take three seconds to record a video and then the video would be logged in your free trial. So it was actually a freemium product that complimented your free trial.

Geoff Roberts: Got it, makes sense. When you talk to early stage SaaS companies today, what are the one or two most common mistakes you see them making when it comes to deciding on a free trial versus freemium model?

Wes Bush: The biggest mistake I see people make is talking to other founders. I know that sounds really weird, but just taking someone else's opinion on what you should do is really a bad framework for deciding what you should do. A lot of other founders are basing what they're recommending on their personal experience and the fact is you have a different business, a different market, and a different audience. There are so many things that you need to look into in order to make an educated decision for yourself.

The biggest mistake I see people make is talking to other founders.
— Wes Bush

Geoff Roberts: One of the things that I think a lot of companies struggle with that do decide to go with a free trial— and something I'm wrestling now with one of our businesses—is do you collect credit card information upfront or at the end of the trial? When does it make sense to ask for payment information upfront?

Wes Bush: As a general rule of thumb I always recommend against asking for the credit card upfront. There's been quite a few studies done about the overall conversion rate, and if you're looking at bottom line revenue it's typically much higher if you don't ask for the credit card right away. You're just going to have more people coming into your free trial, and although the percentage of them who become paying customers is going to be a lot lower, the overall volume is going to be much higher.

However, there are some cases where it makes a lot of sense to collect credit card information upfront. There's companies that deal with a lot of spam and that's a perfect use case—if you get a ton of spammers signing up for your product that's a really good stop gate. Also with products that have a lot of seasonality to them. So let's think of a SEO product, if you’re a one man band or product, then you might just want to do an SEO audit on your site maybe once a year. So you'll just sign up for a free trial and then you'll never come back because you don't want to pay the recurring costs. A lot of these products will see that people are coming back and just using a different email to sign up for the same product. So they’ll just say okay, you’ve got to pay to play because you’ll just keep signing up for this free trial indefinitely unless we add some friction here.

Geoff Roberts: Good point. So for people that decide to go the freemium route, the problem quickly becomes okay, how do I create a sense of urgency in the sales process? We're giving people access to the product for a longer period of time but we still have customer acquisitions goals and need to get buyers to act sooner rather than later. What do you recommend for freemium companies in terms of how they can go about creating that urgency?

Wes Bush: There's a couple ways I've seen companies do it. You don't have to have just a 100% freemium product, you can create a hybrid solution. I've seen companies do this very successfully where they'll lead with the free trial that gives you access to a lot of the key features for 7 or 14 days but then at the end if you don't upgrade, you actually get put on a free forever plan.

For example, Clearbit’s free version goes into your Gmail and enriches your contacts. I thought that was a really smart way of offering a free plan, because it’s essentially free advertising. They sit inside your Gmail and how often do you check your email? If you're a working professional you're in there multiple times each day seeing Clearbit again and again. You should also think about how you can make your freemium product amplify your paid product. So Clearbit sits inside your email and what they're doing is using a lot of your data to enrich their own data. So by giving away a free product Clearbit makes their own paid product more valuable.

But to get back to your question about how do you get people to the upgrade from your freemium product... A big part of it comes down to pricing and if you lead with your product, one of the interesting things is that your customer acquisition model is really tied super closely with your revenue model. If you don't give away a bunch of features, your customer acquisition model suffers because now you have a less powerful offer. On the other hand, if you give away too much and your freemium product has everything people have no reason to upgrade and now your revenue model is shot. You need to fix that and hold back some features, so the best way to look at it from a upgrade perspective is to base your pricing on value metrics.

Patrick Campbell from ProfitWell says there's two types of value metrics, starting with functional value metrics. If I'm Wistia, this is the number of videos you can host on the platform, so you can use that as a value metric. If someone gets three videos uploaded, okay now you're going to have to upgrade and once those three videos are uploaded you should be able to really understand the value of the product anyways. On the other hand, you could use an outcome based approach to value metrics. So it could be how people actually viewed your videos, or how many people came to your website—you're really just trying to pick metrics so that when the product is used you grow with the customer. That's a great way to increase your expansion revenue as well as upgrade rates.

The free trial vs. freemium framework

Geoff Roberts: Awesome. Let’s transition to the free trial versus freemium framework that you shared with me. What is it, why did you develop it, and how do you use it in your day to day work?

Wes Bush: Yeah, so the framework that I built to decide the free trial versus freemium question focuses on four main areas of your business. The first part is your market strategy, so it really focuses on understanding how you want to position your business in the market. For example, say you want to disrupt an existing market dominated by a tool like Adobe Photoshop. Photoshop is really complicated and you can take a full year of learning the program and still have a lot of ways to improve your Photoshop abilities because there’s just a ton you can do with it. But the fact is a lot of people don't actually use anywhere near the full capacity of Photoshop and that's why a company like Canva, which makes it really simple to do graphics, was able to claim huge part of this market.

Second, there's the ocean conditions—is it a really competitive space you're in? If it's a competitive market like say email marketing and everyone has a free trail or freemium offering, it's almost the expectation in the buying process that offer a trial or freemium product. If you're creating a new category, that's a really great place to be but oftentimes a free trial or freemium model isn’t the best fit because you have to educate people so much. It's like Salesforce with the cloud—initially a lot of people didn’t get it. Their sales team had a ton of objections and when you're creating a new category, you actually want to hear those. If you try to automate your entire funnel right away, you're going to miss out on so much valuable feedback.

Next there's the audience are you trying to focus on—do you need a bottoms up or top down approach? What I mean by top down is are you trying to target the executive team, or from a bottoms up perspective are you targeting managers or day to day workers? If you're targeting a top down approach and using a free trial or freemium model, it's going to be pretty hard for those executives depending on how complex your tool is to really get up to value because they're probably not using the tool day to day. A bottoms up approach pairs really well with a free trial or freemium model. That's why you see companies like Slack grow from the bottom. Someone on a development team will say, hey let's start using Slack. They'll send it to a bunch of their coworkers and it spreads internally to other teams. Then when it comes time to upgrade it's really a no-brainer because they already have maybe 30, 40 people on a team who know and love the product and have gotten value out of it.

Then the last part of the framework is time to value. Now if you have a really long time to value, it's going to be really difficult for a free trial or freemium model and I’d actually recommend against it. You want to make sure that your time to value is quick as possible. Freemium models need to be even quicker I'd argue, because you’re using this no hand-holding approach for the most part and you need people to realize value as soon as possible without human intervention. So that's my framework at a high level—I'd love to take your thoughts on it. How did you find it walking through it?

Here are Outseta’s answers to the free trial vs. freemium framework

Geoff Roberts: Yeah, so it made logical sense to me—I sort of understood in most cases what was behind each of the questions. I decided on a freemium model for Outseta for a couple of reasons and your framework gave us a score of 10-2 in favor of freemium, so it validated my thinking in that sense.

A couple of factors that went into that, starting with the market we are selling to. We’re targeting very early stage SaaS start-ups, who are often finding us the day that they open their doors. These companies tend to have very different timelines in terms of when they're going to start using the CRM, versus when they're going to set up the billing system, versus when they want to send their first email campaign. So we wanted to provide enough time for companies to sort of grow into the product and adopt each of its core features as their need for it arose, rather than saying hey you've got 7 or 14 days to kick the tires on all these different aspects of the product.

The second factor is just the product is really big. It's basically three or four well known software categories delivered in one platform and when we think about the onboarding process, everyone's going to start in different place. It's not like everyone wants to send an email campaign first, some people want to start logging deals in the CRM first, some people want to set up billing first. So I felt like we needed to expose people to each of our core features during the onboarding process.

One of our struggles as a result is with people starting at different points, how do we show them value quickly? What action should we present them with first when we don’t know exactly what it is they want to do first? If you look at the initial onboarding screen when you first log in to our product, we say hey you can import your contacts, you can set up your customer support email inbox, you can send an email campaign, author a knowledge based article, each of these being key actions that the product helps with. What’s your take on this approach versus being more specific about what we want users to do?

Outseta’s onboarding dashboard

Outseta’s onboarding dashboard

Wes Bush: I always like to think of onboarding in terms of dominoes—what’s the smallest action you can get people to do that sets them up for success in the future? If you think of Hubspot, it's similar to Outseta in the sense that there's the marketing side and the CRM. Hubspot’s sales product is really great to lead with because it's a Chrome extension that you can setup in less than five minutes. By leading with that product, what happens is your CRM fills up with all your contacts so you now have people to market to. So it's just like a step ladder or you're pushing one domino at a time and it just gets kind of easier as you go.

With your product what I would recommend is seeing out of all the features you have, what is the first thing you need someone to do in order to take them to that next step? Maybe you lead with sales, then you follow up with marketing, and then it's subscriptions or something like that.

I always like to think of onboarding in terms of dominoes—what’s the smallest action you can get people to do that sets them up for success in the future?
— Wes Bush

Geoff Roberts: I think the obvious one is import contacts. You need contacts in the CRM to send an email campaign for example; it’s also what our pricing model is based on. The only case I would say where that probably isn't the right initial action is a company that doesn't have any contacts yet, which is common in our user base, but the domino analogy makes sense.

Wes Bush: Okay, awesome.

Geoff Roberts: So when I went through your framework, one of our answers that came back as “free trial” was based on the size of the total addressable market. If you have a smaller total adjustable market, you’re suggesting a free trial rather than freemium. Why is that?

Wes Bush: One of the problems here is that freemium has a very low conversion rate—typically you'll see anywhere from 1-3% of people who sign up for your freemium product actually turn into a paying customer. So in this case it's a good indicator of saying is your market big enough to support this? If you have a really small market and that low conversion rate of 1-3% percent, you might end up with 100 or 1000 customers and then be capped.

Geoff Roberts: That makes sense. So going back to our own pricing model, one of the pieces of feedback that we've heard about our own pricing is there is a segment of buyers... let's call them solopreneurs, or indie hackers, or makers, who are pretty much unwilling to pay for any product until they get to a point where they're bringing in revenue. They’ll use a Trello board to track their sales process, Hubspot CRM, the free version of MailChimp, and will live with whatever pain exists until they're bringing in money and then will build a real tech stack.

We offer a freemium plan where we give you 250 contacts but access to every feature—the idea here is knowing these businesses have different implementation timelines we give them all the time they need to get everything set up, configure their account, and figure out if they like all the features. Then once they start using the product in earnest, they will very quickly go over that 250 contact limit and upgrade to a paid plan. The feedback we’ve heard is many of these folks intend to go over 250 contacts well before they’re bringing in revenue, so they don't want to incur a $99 per month charge before they really need to.

One experiment we’re considering is giving the entire platform a way for free, but then taking a larger percentage of payments processed through our payment processing system. This would align our pricing model with the most important outcomes based value metric—revenue— and we’d take a cut that's a little bit larger than the 2.9% Stripe charges for example. Curious what your take is here and how we can better appeal to that segment that's very price conscious upfront?

Wes Bush: I definitely recommend leading with whatever that product feature is that's going to help someone get that revenue. So in most cases that's going to be the sales tools and you just want to help them get to the point where they’re willing to pay because your product has helped them generate revenue. I definitely do agree with some of the sentiment around the 250 contacts. In this case I’d definitely think about what are those first tools that you could give people? Maybe you give one of them away for free, it's a sales tool, and then you help them build those contacts so they don’t even have to import any contacts—they’re already there. So then you get that stepping stone where the next upgrade is the marketing product and it’s just a natural extension of the journey.

Geoff Roberts: Yeah that makes sense. I think the other challenge for us is just putting pricing out there that, given the scope of the product, maintains some semblance of simplicity. Contacts seems like a fairly well understood measure of the value people are deriving from the product. What we've heard and seen with our customers is once you move onto our paid pricing plans, the product's a bargain and much cheaper than the competition. The part we’re still wrestling with is that entry level customer and how we can get them in and show them value relatively quickly while still not taking forever for them to upgrade.

Wes Bush: Okay got it.

The start-up scene in Ontario and Wes the bad Canadian


Geoff Roberts: So let’s switch gears a bit—I saw you're in Waterloo, Ontario. What can you tell me about the start-up scene in Waterloo?

Wes Bush: The startup scene in Waterloo is actually really exciting. Out of all the cities in Canada it's has the highest density of start-ups and I think that's really fueled by the fact that there's some really incredible engineering universities around us so there's lots of really great talent that you can hire as a start-up. There’s beginning to be a lot more of these successful companies that are growing and then their employees move on to other companies, build them up, and so what's really exciting about it is just seeing the snowball effect and how it's growing bigger and bigger.

Geoff Roberts: Are you born and raised in Ontario or...

Wes Bush: Yeah, so I was born and raised in Ontario. Have you been?

Geoff Roberts: I haven't, I'm from the Boston area. I've been around Canada quite a bit, but I haven't been to Ontario or Waterloo.

Wes Bush: Make sure you go during the summer.

Geoff Roberts: Yeah, no kidding. What's the most Canadian thing that you love? Are you a hockey fan? What do you love about Canada in general?

Wes Bush: So I feel like I'm not a good Canadian. I don’t like the winter, I'm not big into the sports like hockey. This is not very Canadian at all but I like mountain biking, and forests, and hanging out in the nature, and lakes. There's so many lakes in Ontario. I love that part.

Geoff Roberts: Very cool. If you weren't the free trial versus freemium guy, what else could you see yourself doing? What other direction could you have gone with your career?

Wes Bush: I think I'd still be doing something very similar. I like behavioral psychology, because just figuring out what makes people do certain things and deconstructing it is so fascinating, whether it's deconstructing habits or just why people bought a product online. But yeah I'd still probably be doing something in a similar field.

Geoff Roberts: Outside of work, tell me something else about yourself that your online audience doesn't necessarily know that's going to bring Wes to life.

Wes Bush: So couple things about me, I travel quite a bit. I actually built my business to be location independent, so I'm actually in Thailand right now. I really try to avoid the winter as best as I can and so there's a lot of things I do to just try and explore new places, and try new food at a bunch of these other places which is exciting. I'm also trying to learn how to ride a motorbike. That's fun.

Geoff Roberts: How's the food in Thailand been so far?

Wes Bush: It's really good. I'm not sure if you like Thai food or not-

Geoff Roberts: Love it. How long have you been in Thailand at this point?

Wes Bush: I've been here for a couple months and I usually typically I travel between here or the Los Angeles area so hopefully we can meet up one day in person. And then Toronto, so I kind of make my rounds every year.

Geoff Roberts: Awesome, well that’s all the questions I have for you so I'll let you go. Go get some Thai food! It’s been fun.

Wes Bush: Likewise, thanks so much for having me.

Outseta Company Update - March 2019

By Geoff Roberts 4 min read

Hi-dee-ho! Two months of 2019 are already behind us—here’s an update on what we’ve been cooking up at Outseta so far this year.

New Feature! Lead Capture Form Builder

We’ve long offered forms to help you build your email list as well as product registration and authentication forms that allow users to sign-up or login to your SaaS product. But we recently released a new lead capture form builder to all Outseta customers. Our form builder allows you to generate form code that can easily be dropped into your website pages, or we provide hosted web pages where your form lives as well.

Forms can be customized to capture whatever information you see fit, with form submission data automatically syncing with Outseta CRM records. You can also easily specifiy a post-submission display message or redirect users to a new URL, allowing for easy conversion tracking in Google Analytics or similar tools.

You can learn more about Outseta forms here.


Outseta SaaS Consulting

Throughout the final quarter of 2018 we saw a significant uptick in user engagement with our product. More companies have been signing up for Outseta each month and we’re seeing broader feature usage and more complete implementations of the product than we’ve seen before. We expected that we’d see these signs as the product continued to mature; it’s a pretty good indication that we can prudently start to make more significant investments in growth.

With this is mind, we’re exploring a number of ways to raise some growth capital for the business. A couple of options we’re considering include:

  1. Raising some funding from Tinyseed or Earnest Capital. We shared a post discussing these alternative funding options last month.

  2. Funding the business through revenue from This is a second SaaS project we launched earlier this year, and we’ll be reinvesting the profits into Outseta.

We’ve also taken on some consulting work in the past to provide seed funding for the business. This is something that we’re excited to formalize—we’re committing to helping one company bring a new SaaS product to market each year. If you know a entrepreneur looking for a technical co-founder, a team in need of more development firepower, or any start-up that needs help building their MVP we have a very attractive consulting package to offer.

Here’s the scoop:

We’ll be accepting applications throughout the month of March and will plan on selecting a 2019 project shortly thereafter. See that form at the bottom of the page? That’s one of our new lead capture forms in action.

New Feature! Product Engagement Tracking

While we’ve seen a significant uptick in user engagement with our own product, it was initially a pretty manually process for us to get a sense of which features were being used and how often. Our login forms have always provided some stats on login activity on Outseta’s primary dashboard, but we found ourselves needing to build dashboards in Amazon Quicksight to get better insights into feature adoption and usage.

There are a number of other product engagement tracking tools on the market like Heap Analytics, Mixpanel, and Kissmetrics, but they’re all fairly expensive and overkill for a start-up company. Pretty much every company that’s using Outseta would benefit from better understanding user engagement with their own products, so we built the engagement reports that are the most valuable to early stage start-ups into the platform where they’re nicely tied into the CRM. Outseta customers can now set up and track their own custom events, and can track product engagement based on billing stage, cohort, or month.

For our own use we created custom events that correlate with Outseta’s primary features to help us track events like imported contacts, email campaigns sent, support tickets received, companies that have activated e-payments, and knowledge base articles authored.

Documentation on setting up engagement tracking for your own product is available here.


New Outseta Explainer Video

We recently filmed a new Outseta explainer video that we’re leveraging on our home page. We’re not sharing because this is scintillating creative work—far from it—but as a bootstrapped company we had this video created for $32… Yes, $32. If you’re a start-up in need of an explainer video on the (very) cheap, feel free to reach out and we’ll point you in the right direction.

That’s a wrap!

So who do you know that needs help building a SaaS product?

-Dimitris, Dave, James, & Geoff