Transitioning from Big Tech to Startup Leadership

In this episode of The Tech Trek, Amir sits down with Davy Li, Head of Engineering at Mesa, a startup redefining how homeowners earn rewards on everyday home expenses. Davy shares his personal journey from Big Tech to startup life, unpacks how he’s built Mesa’s engineering team from scratch, and offers a refreshingly candid look at what it means to be an effective leader in a small but growing organization.

From defining cultural values to hiring without a brand name, Davy drops wisdom on leadership, team modeling, and giving engineers the freedom to thrive. If you're building or leading teams in tech—or planning to—this one's packed with insights you can act on today.

🧠 Key Takeaways:

Culture is foundational: Davy built Mesa’s engineering culture before hiring anyone—trust, simplicity, transparency, and bias for action anchor the team.

Give great engineers space: The best devs aren’t waiting on tickets—they’re engaging directly with stakeholders and proposing their own solutions.

Small teams = shared ownership: Davy empowers his team by assigning champions for different technical domains and pushing people outside their lanes.

Startup hiring is scrappy: Without a big brand, Davy had to hustle through referrals and review hundreds of candidates to land A-players.

Upskilling never stops: Whether through reading, podcasts, or trial-by-fire, Davy believes learning is a muscle that needs constant exercise.

🕒 Timestamped Highlights:

(00:40) What Mesa does and how their homeowner rewards work

(02:09) Adjusting from Big Tech to startup: different challenges, different muscles

(03:40) The four cultural values that define Mesa’s engineering org

(06:57) How being closer to the business shifts the way you lead engineering

(09:09) What Davy prioritized when modeling the team from scratch

(11:14) Creating space for engineers to solve real business problems

(13:14) Borrowing from Cash App and Spotify: PR auto-approvals, DRIs, and ownership

(16:50) How Davy closes skill gaps as a manager—and why trying new things matters

(18:31) Promoting psychological safety and cross-functional growth on the team

(21:14) Why he's more hands-on with code now than ever before

(22:47) Startup hiring realities: no brand, no inbound, just grit

(24:55) Best way to reach Davy if you want to connect

💬 Quote to Remember:

“The fastest way to a good idea is to have a lot of ideas—and the fastest way to grow is to just try things.”

🧩 Leadership Tips (from the episode):

• Create psychological safety: Failure should be normalized. That’s how teams experiment and grow.
• Start with culture, not code: Even in the earliest hiring stages, define how you want your team to operate.
• Push responsibility downward: Assign DRIs and let engineers own the full scope of a project—not just the tickets.
• Hire for slope, not just skills: A-players attract A-players, but only if you're willing to dig deep and sell the mission.