Meet Jessica McKellar, CEO and co-founder of Pilot. In this episode, she shares how she built three successful startups, including exits to Oracle and Dropbox, and breaks down why staying close to customers is a must for shaping strategy and culture.

Jessica explains why founders should keep selling long after scaling begins—and how great teams come from values alignment, not titles.

She also reflects on the lessons of being uncool and how empathy, integrity, and curiosity became her biggest superpowers as a leader.