Jessica McKellar's guest appearances

Jessica McKellar

Entrepreneurial Thought Leaders

The Python Podcast.__init__

True Stories of Good People

In Depth

Elon Musk

James Beshara

Marc Andreessen

Julie Zhuo

Sheryl Sandberg

Bonny Simi

Leila Janah

Peter Diamandis

Adam Grant

Guy Kawasaki

David Eagleman

Bryce Dallas Howard

Andre Iguodala

Ben Horowitz

Arlan Hamilton

OwlTail

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. 

Today’s conversation is with <a href="https://www.linkedin.com/in/jesstess/" rel="nofollow" target="_blank">Jessica McKellar</a>, co-founder and CTO of <a href="https://pilot.com/" rel="nofollow" target="_blank">Pilot</a>, 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.

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

Jessica McKellar is the founder and CTO of Pilot, an accounting firm powered by software that has raised more than $160 million in venture capital funding. She also founded Zulip, a group collaboration tool that was acquired by Dropbox in 2014, and Ksplice, which was acquired by Oracle. In this conversation with Stanford adjunct lecturer Emily Ma, McKellar discusses her 15-year journey founding three startups with her co-founders, as well as her passion for creating opportunities for the previously incarcerated. 

Jessica McKellar is the founder and CTO of Pilot, an accounting firm powered by software that has raised more than $160 million in venture capital funding. She also founded Zulip, a group collaboration tool that was acquired by Dropbox in 2014, and Ksplice, which was acquired by Oracle. In this conversation with Stanford adjunct lecturer Emily Ma, McKellar discusses her 15-year journey founding three startups with her co-founders, as well as her passion for creating opportunities for the previously incarcerated.

Jessica McKellar (Pilot) - Serial Co-founders 

Simon Liu

Tenzin Kyizom

For formerly incarcerated individuals, safe, stable and affordable housing is the foundation of a smooth reentry into society. Unfortunately, it’s often the most difficult resource for them to obtain. Recognizing this need, one San Francisco Bay Area collective—run by and for formerly incarcerated Californians—is bringing housing and other necessary resources to people who have been similarly impacted by the criminal justice system. Not long ago, a collective member purchased a house where people who have recently been released from prison can live while they get back on their feet.

For formerly incarcerated individuals, safe, stable and affordable housing is the foundation of a smooth reentry into society. Unfortunately, it’s often the most difficult resource for them to obtain. Recognizing this need, one San Francisco Bay Area collective—run by and for formerly incarcerated Californians—is bringing housing and other necessary resources to people who have been similarly impacted by the criminal justice system. Not long ago, a collective member purchased a house where people who have recently been released from prison can live while they get back on their feet.

Bay Area Freedom Collective: Simon Liu, Jessica McKellar & Tenzin Kyizom