The Peterman Pod Ex-Stripe CTO on What Grew His Career, Hiring Without Leetcode, Coding as a Leader (Career Story)
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Aug 29, 2025 David Singleton, the former CTO of Stripe and ex-VP at Google, shares his remarkable journey from junior engineer to tech leadership. He discusses innovative hiring practices at Stripe that bypassed the traditional Leetcode approach. Singleton emphasizes the necessity for engineering leaders to maintain coding skills and provides insights into effective communication and team culture in remote settings. He also reflects on personal growth, the pivotal book that shaped his career, and his new venture in building AI platforms for consumers.
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How Programming Started For David
- David taught himself to code by building invoicing software for his parents that replaced their manual bookkeeping.
- That early impact convinced him software could help many people and led him to study CS and pursue software professionally.
Learning From Symbian Field Work
- At Symbian David worked as a technical consultant embedding with handset teams across Panasonic, Samsung, and Nokia.
- The role taught him how team culture and organization directly shape deliverables and engineering outcomes.
Stay Where You Keep Learning
- Stay where you learn the most; David stayed at Google nearly 12 years because he kept learning new domains.
- Treat roles as learning opportunities and rotate into areas that stretch you every 18–24 months.
