Naval Aviator to SaaS CEO: Glenn Weinstein on Leadership, Scaling, and Serving Developers

#006:  In this episode of DevEx Unpacked, Cloudsmith co-founder Alan Carson sits down with CEO Glenn Weinstein for a deep dive into leadership, growth, and developer-first thinking. Glenn shares his journey from programming on a Commodore PET to founding and selling a startup, his lessons from Twilio, and what drew him to lead Cloudsmith. The two discuss what it takes to build a category-defining company from Belfast, navigating VC funding, and how values like resilience, clarity, and service drive long-term success.A must-listen for founders, tech leaders, and anyone scaling with purpose. (00:00) - Introduction (08:17) - Building and Exiting a Startup: The Appirio Journey (12:10) - Lessons from Twilio and Why Cloudsmith Stood Out (15:46) - Becoming Cloudsmith CEO: Conviction, Relocation & Responsibility (20:06) - Naval Training Meets Startup Life: A Blueprint for Leadership (23:24) - Inside the Cloudsmith Offsite: Culture, Awards & Team Spirit (29:07) - Comfort vs. Conviction: The Pressure of Leading a Start-up (34:40) - Persistence, SDRs, and the Power of Trying Again (37:03) - Silicon Valley Is an Idea, Can Belfast Replicate It? (41:33) - Why Series B Matters: Signaling Strength to the Market (46:07) - IPO Ambitions and Staying True to Developers (47:56) - Serving Developers Is Serving the Enterprise