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Becoming a better strategic contributor & business leader

with Jessica McKellar

August 17, 2023
Becoming a better strategic contributor & business leader
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Jessica McKellar (@jessicamckellar) is a repeat founder and the CTO of fintech unicorn Pilot, an accounting firm powered by software.

Previously, she was a founder and the VP of Engineering for Zulip, a real-time collaboration startup acquired by Dropbox, where she then served as a Director of Engineering. Before that, she was a computer nerd at MIT who joined her friends at Ksplice, a company building a service for rebootless kernel updates on Linux that was acquired by Oracle.

Jessica is a former Director for the Python Software Foundation and PyCon North America Diversity Outreach Chair. For her outreach efforts in the Python community, she was awarded the O'Reilly Open Source Award.

Open source meets criminal justice reform in Jessica’s work with The Last Mile, a job training and re-entry program that has implemented the first computer programming curriculum inside US prisons. She teaches Python at San Quentin State Prison in California, hires formerly incarcerated software engineers, and uses that bridge between the tech industry and prisons to get people activated and acting for decarceration.

"You need to be able to think about the business in a way where you have ideas that inflect the business. What is a gap in the product that needs to be addressed? What's an idea for a way to achieve a step function improvement in margin? How can we save the company money that it is spending via an engineering investment?

<cite>- Jessica McKellar   </cite>

Join us at ELC Annual 2023!

ELC Annual is our flagship conference for engineering leaders. You’ll learn from experts in engineering and leadership, gain mentorship and support from like-minded professionals, expand your perspectives, build relationships across the tech industry, and leave with practical prove strategies.

Join us this August 30-31 at the Fort Mason Center in San Francisco

For tickets, head to https://sfelc.com/annual2023


  • Jessica’s founder story @ Pilot (3:26)
  • How founding Pilot is different from past experiences w/ Zulip & Ksplice (4:29)
  • The story behind Pilot’s “power team” of founders (7:06)
  • Distinctions between Jessica’s focus as CTO / founder & eng roles (11:36)
  • How eng functions can help the exec team hit important metrics (14:40)
  • Daily actions that help optimize & monitor metrics like margin (16:33)
  • Frameworks for identifying business trajectory (19:46)
  • What parts of business-building discipline need to be prioritized long-term (21:29)
  • Use market fit & size of market to determine your company’s goal end state (22:48)
  • Past lessons the founding team applied while starting Pilot (24:45)
  • Things Jessica thinks she & her co-founders do right (25:23)
  • Recommendations for exploring potential paths & aligning on the final decision (29:20)
  • Steps for becoming a more impactful, strategic business contributor (30:55)
  • How eng leaders can identify ideal end state & achieve product-market fit (35:15)
  • Create collaboration between product, eng & design teams (37:28)
  • Rapid fire questions (37:09)


  • Cool People Who Did Cool Stuff - This weekly podcast dives into history to drag up the wildest rebels, the most beautiful revolts, and all the people who long to be—and fight to be—free. It explores complex stories of resistance that offer lessons and inspiration for us today, focusing on the ensemble casts that make up each act of history.
  • And Away… - Bob Mortimer’s life was trundling along happily until suddenly in 2015 he was diagnosed with a heart condition that required immediate surgery and forced him to cancel an upcoming tour. The episode unnerved him, but forced him to reflect on his life so far. This is the framework for his hilarious and moving memoir, And Away…

This episode wouldn’t have been possible without the help of our incredible production team:

Patrick Gallagher - Producer & Co-Host

Jerry Li - Co-Host

Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/

Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/

Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/

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