Someone asked me recently what keeps me up at night after 8+ years as a Founder. As my brain sought an answer I realized that I was mentally running through a list of the usual suspects—none of which really fit. Yet, I absolutely knew the answer.

• It’s not Co-founder drama.
• It’s not running out of money.
• It’s not the potential for downtime while running a piece of software that’s critical infrastructure for our customers.
• It’s not competing with bigger and better funded competitors.
• It’s not AI and the rapidly changing landscape of how software is built...

What keeps me up at night is the possibility that I’m thinking too small and missing an opportunity to go much bigger with Outseta.

I want to make sure that we're at the very least realizing a healthy percentage of our potential, because damn we've worked hard for it. I feel a strong sense that I owe that to our team, to our customers, and also to myself.

I’ve always had this feeling to some extent, but it’s actually grown as Outseta has become more successful. As I’ve been able to look at the product now after 8+ years and truly feel that we’ve built something that’s both unique and objectively good.

I don’t mean “go much bigger” in the sense of we should raise money and go faster.

I mean it almost entirely in terms of how we’ve positioned Outseta—and I think it keeps me up so much because I’m the “Marketing Founder” and I generally see positioning as one of my strengths. But I genuinely believe that Outseta is a very tough product to position well—and I have a strong sense that our current positioning isn’t maximizing our potential. I want to know that we're positioning Outseta is a way that:

• People "get it" quickly
• We're addressing the largest swath of the market possible
• Our messaging "hunts" effectively in a way that maximizes our growth potential

While you see a lot of “membership software” language on our website, that’s very much a compromise—I didn’t want to create a category and “membership software” is the pre-existing, well understood category of software that Outseta fits into most neatly. Many of our customers charge membership fees and are building protected content use cases… but nearly as many are building SaaS products or other types of digital businesses and the membership software language is actually a turn off to them.

The truth of the matter is that at its core Outseta is a payments and authentication platform, but it’s wrapped in CRM, email, and help desk tools too. It’s a suite of tools that you’ll inevitably need to run many types of small, digital businesses. And we’re a platform that spans a whole bunch of well understood and insanely competitive software categories—what’s most unique about us is that we bring it all together (and what that enables).

I try to explain all of this on our "Is Outseta for me?" page, but I need the 5-word positioning that maps to this full page.

Outseta is dramatically different from the other membership software providers—and in so many ways we’re underselling what we offer. There are really very few products that offer the combination of tools that we do—the closest is definitely Hubspot. Outseta is very much a more lightweight version of Hubspot in terms of our CRM, email, and help desk features, with a much greater emphasis on payments and authentication. We don’t want to be Hubspot—we intentionally want to play very downmarket from them. But if they can make $2.63B annually (2024) then fuck—I have to think we can make $20M. From a product perspective, the “core” of what we need to get there is already there.

I have lots of ideas of how this could be positioned, but not a lot of conviction on any specific direction quite yet. And the positioning aside, there’s a whole other track of mental work in thinking through “OK, what else needs to change strategically to go much bigger, much faster?” As I’ve been in the depths of this business for 8+ years, I know I could use some mental sparring partners there.

It’s not that I haven’t pursued this. The most impactful mentor in my marketing life was the CMO who took Constant Contact from a start-up to $250M in annual revenue. I never call on her unless I really need some guidance, and she’s particularly strong in positioning. As we talked through this, her response summarized was “Damn, Geoff—this is a really hard problem.” Sometimes that’s actually what great mentors do. 

One idea that I keep coming back to is something akin to “Full-stack Stripe.” This is the wrong terminology as “full-stack” means something very different to developers, but what I mean by this is positioning Outseta as the complete tech stack for small businesses who want to sell digital products via Stripe. Not in a “we want to be a digital storefront” way, but more in a “you want to sell your product via Stripe and we give you the full stack of tools that will help you build a more successful business” way.

This is what we do, but it’s a hard thing to communicate well and we lose the benefits of positioning ourselves in a category that’s already well understood to potential customers.

Anyways, that’s what keeps me up at night!

And as Outseta has moved across the spectrum of survival > default alive > to growing, this is what I find myself wrestling with more and more. Am I thinking too small? How can we go much bigger? And what can we do to maximize the upside that this whole team has worked so hard for?