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 6 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, and both netted some 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. 

Engaging conversation with Jessica McKellar, Andrew Lau, Samir Naik, and a former VPE at Robinhood about aligning engineering with business goals, team topologies, and strategic thinking in engineering leadership. Insights on metrics tracking, org design during hyper-growth, and optimizing virtual teams for customer focus.

Jessica McKellar, CTO & Founder @ Pilot, shares strategies for achieving product-market fit, measuring important metrics, prioritizing long-term business building disciplines, and fostering collaboration between product, eng, & design teams. They discuss understanding the business trajectory, building business discipline, tracking metrics, assessing business tools, and trends like decarceration in California.