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Awarded Best of Apple Podcasts, The $100 MBA Show delivers practical business lessons for the real world. These no fluff episodes are packed with only the pure business building training you want. Omar Zenhom shares lessons, strategies and insights from 20+ years of entrepreneurship. He’s bootstrapped two multi-million dollar businesses (and several smaller businesses, too). Join him for short, actionable lessons on how to do everything from validating your idea, to audience-building and mar ...
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What happens when you stop treating HR as a back-office function and start designing it as a competitive advantage?
Theresa Cantwell, Strategic HR Consultant and Director at GSD HR Consulting, believes scaling a company shouldn't mean burning out your team—or yourself. With nearly two decades leading people strategy at companies like Microsoft, ThoughtWorks, and Equal Experts, Theresa has helped organizations across Europe and Asia grow not just fast, but gracefully.
In this episode, we dive into the most overlooked challenges founders face when they scale: losing visibility, clinging to control, and skipping the crucial step of designing people and culture systems that can actually support growth. From shadow planning and succession strategies to why success itself can be terrifying, Theresa shares powerful tools and real talk every startup leader needs to hear.
If you're moving past 20 employees and want to build a company that lasts—without losing what made it special—this conversation is your playbook.
Key Takeaways
- Start HR Strategy Early: Don’t wait for burnout or lawsuits—build people ops into your scaling strategy from day one.
- Shadow Planning Is Essential: Prepare for the worst by confronting your team’s shadow behaviors and stress reactions before they sabotage growth.
- Succession Planning Isn’t Personal: It's about scalability. Delegate early, document processes, and regularly revisit org design.
- Growth Changes Everything: Founders need to let go to level up. What got you here won’t get you there.
- AI in HR Is a Tool, Not a Fix: Automate the repetitive, but double down on building trust and strategic visibility.
Additional Insights
- HR should be the connective tissue of an organization—not the "issues and tissues" team.
- Scaling gracefully requires confronting the emotional toll of growth, including fear of success.
- Theresa shares how early experiences at Microsoft and ThoughtWorks shaped her belief in high-trust, high-agency cultures.
- Executive coaching and intentional design can prevent burnout and boost retention.
Episode Highlights
00:00 – Episode Recap
Theresa Cantwell unpacks the emotional complexity of growth—from the fear of success to the need for intentional HR design. With experience scaling organizations across continents, she shares how founders can build people-first cultures that thrive under pressure.
01:54 – Guest Introduction: Theresa Cantwell
Theresa is a strategic HR consultant and founder of GSD HR Consulting, with nearly two decades of experience building and scaling agile-aligned cultures in the tech and digital sectors.
04:43 – Pivotal Moment at Microsoft
Seeing a team she’d hired bonding over lunch sparked her transition from recruitment to building cultures that last.
06:28 – ThoughtWorks and Radical Culture Design
Barry reflects on his own onboarding experience and how Theresa helped him understand the unique culture of ThoughtWorks from day one.
09:33 – From Recruiter to Culture Architect
Theresa shares why she shifted from acquisition to engagement, building full lifecycle HR strategies rooted in trust and clarity.
15:29 – When to Start Thinking About People Strategy
At 20 people, you need to get intentional—mission, values, cofounder conflict prep, and hiring bar must be aligned.
18:51 – Shadow Planning Explained
Why leaders must confront their own stress behaviors and prepare for the worst—before it happens.
22:39 – Handling Employee Departures with Grace
How to de-risk talent exits through succession planning and constant market awareness.
26:39 – Scaling Yourself Out of a Job
Helping leaders delegate, prevent burnout, and imagine new roles for themselves as the company grows.
32:16 – When to Start Succession Planning
The earlier, the better—start once you have traction. Document, delegate, and depersonalize the process.
36:17 – AI’s Role in HR
AI can’t replace the human heart of HR—but it can free you to focus on what matters most.
38:50 – Closing Reflections
Barry praises Theresa’s impact and encourages founders at scaling junctures to seek her wisdom and services.
Useful Resources
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