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 leadershipWhat she learned at MySpace during the Facebook takeoverThe Reed Hastings quote that changed how she viewed mediaHow startups should think about building culture at scaleThe real impact of trusting your gut during hiring decisionsWhy she values athletes and first-job hustle when building teamsTips for creating aligned, global cultures across multiple time zonesTimestamps: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 ThoughtsPlus, 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.🔗 Don’t forget to rate, review, and subscribe on Apple, Spotify, or YouTube! Hosted on Acast. See acast.com/privacy for more information.