Naval Aviator to SaaS CEO: Glenn Weinstein on Leadership, Scaling, and Serving Developers
May 29, 2025•49 min
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Episode description
#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
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