DevEx Unpacked

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

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#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
    • ...more
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