What this 3-time founding team did differently to find product-market fit faster — Jessica McKellar, CTO of Pilot

**Jessica McKellar** (0:01)
Customers kept coming back to us saying, can you do more for me?
Can you also do my taxes? And this is the other thing that's really attractive about bookkeeping as an entry point to the back office. There is a bunch of really natural expansion out of bookkeeping. So first, it's attractive to the customer to have all of this under one roof. Who's doing your books? Who's doing your taxes? Who's your strategic advisor or fractional CFO? Who's handling your R&D tax credits? Yeah, for sure. If you can get that all done under one roof and you don't have to deal with and coordinate amongst multiple vendors, awesome. So I think there's synergy on the product. It's a better customer experience.
Getting that poll of, hey, can you do X for me? Can you do Y for me?
Suggested that, yeah, we were actually providing a customer experience that was so valuable that people wanted to not just pay us for bookkeeping, but actually to expand the engagement with us.

**Brett Berson** (0:54)
Welcome to In Depth, a show that surfaces tactical advice, and helps us understand what the founders and startup leaders need to grow their teams, companies and themselves. I'm Brett Berson, a partner at First Round, and we're a venture capital firm that helps startups like Notion, Roblox, Uber and Square, tackle company building firsts. On the In Depth podcast, we share weekly conversations with startup leaders that skip the talking points and go deeper into not just what to do, but how to do it.
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**Todd Jackson** (1:30)
Hey everyone, welcome to In Depth. I'm Todd Jackson and I'm a partner here at First Round. I'm back guest hosting a new episode in our series that explores founders' different paths to product market fit. Today's conversation is with Jessica McKellar, co-founder and CTO of Pilot, which is the largest accounting firm for startups. She's been working on Pilot for the last six years with her two co-founders, Waseem Daher and Jeff Arnold. But what makes this founding trio super unique is that they've stuck together in not just one, but three different startups.
As repeat founders, the Pilot team has learned a ton from their first two ventures, K Splice and Zulip, which both netted positive outcomes. But as Jessica will share today, there were mistakes the team made along the way that prevented both products from becoming an outsized success.
So she unpacks what they did differently with Pilot, particularly when it came to picking an acute problem and a huge market to tackle. Jessica also shares the tedious process for building the early version of the product, which included looking over Waseem and Jeff's shoulders as they manually did the bookkeeping for early customers while she wrote code alongside them. Even going back to the earliest days, Pilot had some really strong product market fit signals, with customers agreeing to pull out their credit card and pay for the product right away when it was just an idea on paper, and eventually pulling the Pilot team into expanding their product suite. Make no mistake about it, being a founder is incredibly difficult, but choosing the right problem to tackle can drastically smooth the path ahead of you. I hope you enjoy this conversation with Jessica.
So today I'm joined by Jessica McKellar, the founder and CTO of Pilot, a bookkeeping platform for startups and small businesses. Pilot was founded in 2017 and is now the largest accounting firm for startups in the US. They hit unicorn status in 2021 and have an incredible set of investors, Sequoia, Stripe, Index, and a long list of great folks. And Jessica is a three-time founder and has started all three companies with the same two co-founders, Jeff Arnold and Waseem Daher. And I had the opportunity to work with Jessica, Jeff, and Waseem at Dropbox, so I'm super excited to dig into Pilot's founding story today. Jessica, welcome to the show.

**Jessica McKellar** (3:44)
Thank you so much for having me.

**Todd Jackson** (3:46)
So you've now started three companies together with Jeff and Waseem. K Splice, which I know you sold to Oracle, and Zulip, which you sold to Dropbox, that's how we met. Tell me about your co-founders, how you met them, and why you seem to love starting companies together so much.

**Jessica McKellar** (4:00)
I've known them for longer than I've known my husband. So some of the longest relationships that I've had in my life are with Jeff and Waseem. So we were all computer nerds at MIT.
We met in MIT's computer club called SIPI, the Student Information Processing Board, which is a callback to when there was like a timeshare computer system that you had to reserve time on. And this was the club that helped allocate that time. The nerdiest of the computer nerds hung out at the computer club and that's where we met.