Trust Your Instincts: Building Culture, Teams & Career Success with Lin Cherry

In this episode of Hire Learning, host Oz Rashid sits down with Lin Cherry, a powerhouse executive with experience as Chief Legal Officer and Chief People Officer in fast-growing tech and media companies. From her early days at MySpace to building high-impact legal and HR teams at Wiseline, Lin shares a career filled with bold transitions, leadership insights, and instinct-led decision-making.

🔥 Topics Covered:

• The surprising connection between legal strategy and people leadership
• What she learned at MySpace during the Facebook takeover
• The Reed Hastings quote that changed how she viewed media
• How startups should think about building culture at scale
• The real impact of trusting your gut during hiring decisions
• Why she values athletes and first-job hustle when building teams
• Tips for creating aligned, global cultures across multiple time zones

Timestamps:

0:00 - Intro: Meet Lin Cherry

2:12 - New Year’s Resolutions & Family Reflections

4:45 - From CLO to CPO: How Legal Led to People Leadership

7:18 - Legal Strategy Meets People-Centric Culture

9:44 - Why Wiseline Handpicked Lin to Lead HR

13:06 - Lessons from MySpace vs. Facebook: Tech & UX

17:48 - Reed Hastings’ Quote That Nailed Media’s Future

20:55 - Why Tech Companies Win at Content Distribution

25:34 - Creating HR & Legal Harmony in Startups

28:56 - Lin’s Hiring Philosophy: Mindset > Skillset

32:12 - What First Jobs Teach You About Grit

35:47 - A Memorable Interview Mistake

38:18 - Creating a Great Candidate Experience

41:05 - Best Hire She Ever Made—And Why

43:22 - Wicked, Hamilton & Content That Changes Perception

45:39 - Book Recommendation: Amy Edmondson on Failure

47:30 - Advice to Her 20-Year-Old Self

49:12 - Florida Speed Round: Food, Travel, and Disney Picks

53:15 - Wrap-Up & Final Thoughts

Plus, Lin reflects on the biggest lesson she’d give her 20-year-old self: trust your instincts—even when you're the only woman in the room.

🎯 Whether you're in HR, legal, or leadership, this episode will give you an edge in building smarter, more human-centric teams.

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