In this raw and insightful episode of Software Leaders Uncensored, host Steve Taplin sits down with Jason Tesser, a five-time founder and now CTO/ VP of Engineering at Revvable, to discuss the highs and lows of engineering leadership. Jason shares lessons from his 25-year tech journey, including why data engineering is often the Achilles’ heel of scaling software, how he rebuilt Revvable’s dev team with clear roles, and how a simple autofill Chrome extension disrupted an overlooked industry. Plus, he opens up about job market struggles—applying to 450 roles before finding the right fit—and the importance of staying hands-on, even at the top.