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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