191: How This COO Systematized Scale Without Losing Culture | Gwen Tormey

Winning companies aren’t just built on strategies—they’re built on trust, curiosity, and culture. 

In this dynamic episode, host Damon Lembi sits down with Gwen Tormey, COO of Corestream, who helped the company scale from scrappy startup to award-winning employer. Gwen shares how she architected a resilient operating system and an inclusive, people-first culture while quadrupling the size of her team. They dive into practical frameworks like OKRs and the 4 Disciplines of Execution (4DX), discuss building psychological safety, and swap stories about hiring, AI adoption, and empowering employees to innovate from any seat. Whether you’re scaling a business or leading a small team, you’ll come away inspired with actionable tools to elevate your leadership and your culture. 

In this episode, you’ll learn: 

• How Gwen prioritized both operations and culture by listening deeply before leading change 
• The art and discipline of incubate, then delegate—and how to turn quick wins into lasting systems 
• What Gwen learned from her own startup journey (and why product-market fit and business model matter) 
• Corestream’s step-by-step OKR and 4DX mashup—and how it powers alignment across the org 
• How to hire A-players and build psychological safety (using the Who hiring methodology) 
• Why innovation and process optimization can go hand-in-hand with a people-first mindset 
• Practical strategies for driving AI adoption—from team hackathons to hands-on experiments 

Timestamps: 

00:00 – Why it’s okay to fail and the power of positive reinforcement 

00:16 – Meet Gwen Tormey: From startup to scaling COO 

01:21 – How Gwen balanced building operations and culture 

02:36 – Why trust and curiosity beat quick fixes for new leaders 

04:26 – “Incubate then delegate”: Gwen’s approach to operational leadership 

07:54 – Lessons learned from launching Footstep Labs 

11:57 – What founders need to know about business models and product-market fit 

13:54 – How Gwen mentors startups: Pessimism meets idealism 

14:28 – Breaking down Corestream’s OKR + 4DX execution engine 

17:02 – How company-wide goals connect individuals to the North Star 

19:54 – The tools, reminders, and culture needed for successful OKRs 

22:28 – Building psychological safety and rewarding humility 

25:55 – Shifting culture: New hiring, new values, and a “culture council” 

28:46 – Gwen’s take on work samples and thorough hiring 

31:08 – Why optimizing processes empowers people—never replaces them 

32:38 – Getting frontline teams to embrace process improvement and AI 

35:04 – Gwen’s best AI adoption tip: Hackathons and hands-on coaching 

37:07 – Should you mandate AI tools? Building a flexible, supportive policy 

39:29 – The hardest part of scaling culture: Communication and breaking silos 

42:15 – What excites Gwen about Corestream’s future 

About Gwen Tormey 

Gwen Tormey is the Chief Operating Officer of Corestream, where she’s engineered the company’s rapid growth and helped quadruple the team size, all while securing multiple workplace culture awards. Gwen brings a diverse background as a founder, investor, and operational leader, blending deep curiosity and systems thinking with a relentless focus on people. From rebuilding account management from scratch to designing innovative ways to hire, empower, and retain A-players, Gwen’s signature is bridging operational rigor and human-first values. 

Resources & Mentions 

• Gwen on LinkedIn 
• Objectives and Key Results (OKR) framework 
• Who: The A Method for Hiring 
• Skunk Works — What Is It? 

Podcast Contact Information: 

Website: www.learnit.com 

Email: podcast@learnit.com 

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