Becoming a better strategic contributor & business leader w/ Jessica McKellar

In this episode, Jessica McKellar, CTO & Founder @ Pilot, shares her story as a serial founder and the lessons that can help you become a more impactful, strategic business contributor & eng leader. She reveals strategies for identifying your company’s ideal end state & the steps needed to achieve product-market fit, daily practices that help measure important metrics, business-building disciplines that need to be prioritized long term, and steps for creating positive collaboration between product, eng & design teams.ABOUT JESSICA MCKELLARJessica 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?- Jessica McKellar  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 FranciscoFor tickets, head to https://sfelc.com/annual2023SHOW NOTES:Jessica’s founder story @ Pilot (3:04)How founding Pilot is different from past experiences w/ Zulip & Ksplice (4:07)The story behind Pilot’s “power team” of founders (6:44)Distinctions between Jessica’s focus as CTO / founder & eng roles (11:14)How eng functions can help the exec team hit important metrics (14:18)Daily actions that help optimize & monitor metrics like margin (16:11)Frameworks for identifying business trajectory (19:24)What parts of business-building discipline need to be prioritized long-term (21:07)Use market fit & size of market to determine your company’s goal end state (22:26)Past lessons the founding team applied while starting Pilot (24:23)Things Jessica thinks she & her co-founders do right (25:01)Recommendations for exploring potential paths & aligning on the final decision (28:58)Steps for becoming a more impactful, strategic business contributor (30:33)How eng leaders can identify ideal end state & achieve product-market fit (35:15)Create collaboration between product, eng & design teams (37:06)Ra