Annie Wickman shares insights from her journey as Google alum, first non-founder at Humu, and now Head of People at Character AI. Annie tackles our hardest questions in an unmissable episode. She covers the tensions between product-market fit and company culture, Character AI's unprecedented Google deal structure, taking the leap from people leader to a VC, and how to rebuild organizational trust.

*Email us your questions or topics for Kelli & Nolan: hrheretics@turpentine.co

For coaching and advising inquire at https://kellidragovich.com/

HR Heretics is a podcast from Turpentine.

Support HR Heretics Sponsors:

Planful empowers teams just like yours to unlock the secrets of successful workforce planning. Use data-driven insights to develop accurate forecasts, close hiring gaps, and adjust talent acquisition plans collaboratively based on costs today and into the future. ✍️ Go to https://planful.com/heretics to see how you can transform your HR strategy.

Metaview is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/heretics

KEEP UP WITH ANNIE, NOLAN + KELLI ON LINKEDIN

Annie: https://www.linkedin.com/in/annie-wickman-3332731/

Nolan: https://www.linkedin.com/in/nolan-church/

Kelli: https://www.linkedin.com/in/kellidragovich/

—

LINK/S:

Character.AI: https://character.ai/

—

TIMESTAMPS:

(00:00) Intro

(01:17) Experience as First Non-Founder at Humu

(03:16) Early Employee Challenges & Responsibilities

(05:03) Why Annie Stayed at Humu for Four Years

(06:30) Product Market Fit vs. Company Culture

(09:05) When to Invest in Culture

(11:15) Hiring the Right Leaders for Company Stage

(11:40) Maintaining Morale When Company Isn't Winning

(12:42) Transparency as Trust Builder

(13:47) Sponsors: Planful | Metaview

(16:47) Rebuilding Trust Through Honest Communication

(19:11) Laszlo's Leadership Philosophy: Stretching People

(21:02) Annie's Experience in Venture Capital at Forerunner

(23:12) Teaching Founders to Fish vs. Providing Services

(24:51) How to Evaluate VC Opportunities

(26:09) Understanding VC Economics and Carry Structure

(30:10) Character AI's Unprecedented Google Deal

(32:56) Rebuilding Post-Acquisition: Product Vision Challenges

(34:13) Annie's Perspective on the Deal Timeline

(37:31) Post-Deal Reset: Napa Offsite and Hackathon

(39:29) Employee Ownership After Acquisition

(41:29) Building a New Culture While Keeping the Brand

(42:11) Wrap

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com