How we made our first sale as a startup

We worked on onboarding automation for fintechs throughout the YC F24 batch and made reasonable progress. We made our first sale the week before we flew to SF.

It was pretty simple. We saw there were some old companies in the space building the rule engines that fintechs use to determine whether to approve or deny a sign-up (for fraud/compliance reasons). We thought we could do this better with AI (though not clear how) and that it’d be faster to try sell this to early-stage companies.

We went on LinkedIn and reached out to about 100 operations leaders at early-stage fintechs (15-50 headcount). We got a bite from a small payment provider based in the UK. Here’s the message we used.

First call

We hopped on a call with them that week. They wanted to launch self-serve onboarding and had a super manual process of onboarding customers over email. They said they wanted to get this sorted that quarter. The timing was perfect.

Second call

After a bit of follow-up, they looped in the CEO, who asked us a few more questions about our background. We demoed a front-end version of our drag-and-drop signup form builder + rule engine, said it worked, and that we knew what we were doing.

“Let’s do it”

I couldn’t believe that was enough to land a 2000 USD / month contract within a week. We agreed to help them analyze their onboarding data, come up with a good sign-up flow, decide on approve/deny rules to implement, and build everything.

They wanted a consultancy/dev shop—it was definitely more of a services contract. We were content either way and thought we were “off to the races”. 100 outbound messages = a 2k contract? This was going to be easy…

We sent them a Stripe invoice link that day and the invoice was paid the following day. I remember it feeling almost underwhelming at the time. I didn’t feel as ‘happy’ as I thought I would as my goalpost immediately shifted to closing the next sale.

But after weeks of that same process, days of long and mind-numbing outreach, we couldn’t replicate it. We managed to sign some contracts towards the end of the batch (although I’m pretty convinced they did it as a favor to us with demo day coming up), lost conviction, and decided to pivot. That’s a story for another time with a bunch of learnings.

First sale with Autumn

With Autumn our approach was less sales-heavy from the start. We just wanted to talk to founders and see what their problems were. This time we had the YC community at our disposal, so emailed about 150 founders of product-led companies to chat about the tools they used. We knew we wanted to try building in that space, optimizing for a company we’d enjoy building as this is what we struggled with when building Recase.

One fairly high-profile company responded and mentioned that billing was a nightmare for them. Their users paid for credits, and they wanted a system that could outsource all the credit balance and payment logic.

After speaking to a few more founders we decided to mockup a prototype in a Figma alternative (Subframe), went back to this same founder, and presented it. He was super chilled and agreed to pay us 400 USD a month for it.

If I had to pay forward the learnings from my very nascent sales career it would be:

• You probably don’t need to write any code to sell something. But you almost definitely need to show something that demonstrates you can solve the problem. That can be a mockup, but think about who you’re demoing to. Are they a founder who is okay with seeing something early? Are they a compliance person who need to get the impression of a fully formed product to take a chance?

• Getting the first sale can be pretty easy if you talk to people and stumble on an acute problem someone has at the right time.

• The question is whether multiple people fit that same persona, have the same problem, and want the same thing. It’s tempting to get that sale and run 100% towards it which is the approach we took, but a ‘safer’ one is probably to make multiple sales before building. People who tried to build in this space and failed advised us to do exactly this. If you can do this you’ve likely uncovered the makings of a massive company. The trade-off is you’ll likely spend a lot longer in the idea maze (aka pivot hell), which can be shit.

It’s been 8 months for us and we’re still figuring it out. You decide what works best for the company you want to build.