“HR Heretics” | How CPOs, CHROs, Founders, and Boards Build High Performing Companies

HR Heretics
“HR Heretics” | How CPOs, CHROs, Founders, and Boards Build High Performing Companies

After a decade+ of “blitz-scaling” companies, HR, talent, and People leaders now face an uncertain economy that has already seen big booms and busts. What will it take to construct the next generation of incredible businesses – and where can people leaders have the most business impact?     Hosts Nolan Church and Kelli Dragovich have been through it all, the highs and the lows – IPOs, layoffs, executive turnover, board meetings, culture changes, and more. With a lineup of industry vets and experts, Nolan and Kelli break down the nitty-gritty details, trade offs, and dynamics of constructing high performing companies. Through unfiltered conversations that can only happen between seasoned practitioners – Kelli and Nolan dive deep into the kind of leadership-level strategy that often happens behind closed doors. This show is for those who are ready to ditch conventional wisdom and figure out from first principles what works for their culture, business model, and industry, with the goal of building a resilient and enduring company. You’ll come away with real guidance for seeing around corners, building enduring companies, and carving out an impactful career – plus a newly-honed bullshit detector. Topics frequently touched on in this season include: building high performing cultures, compensation negotiation, performance reviews, company design, equity, M&As, recruiting the best talent, and how to manage your own psychology as a people leader. hrheretics.substack.com

  1. 1D AGO

    Sapphire VC’s People Leaders Retreat & Deep Fakes

    Kelli and Nolan recap their experience at the recent Sapphire People Leader Retreat focused on the evolving role of CPOs in 2025, covering executive alignment, moral boundaries, burnout prevention, and peer networks. They also share a case of corporate identity theft targeting job candidates, highlighting emerging recruitment security challenges. *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 NOLAN + KELLI ON LINKEDIN Nolan: https://www.linkedin.com/in/nolan-church/ Kelli: https://www.linkedin.com/in/kellidragovich/ TIMESTAMPS: (00:00) Intro (02:10) The Role of CPO in 2025 (02:20) Corporate Deep Fake Fraud Story (03:30) How the Deep Fake Was Discovered (04:00) FBI Involvement & Next Wave of Fraud (05:10) Pelion VC Domain Fraud Case (05:50) Value of Raw Conversations at Retreat (06:10) No One-Size-Fits-All CPO Role (07:00) Executive Alignment Importance (08:30) Sussing Out Cultural Fit (10:10) Moral Boundaries vs. Running Experiments (12:00) Learning from Radical Ideas at Carta (12:30) "Care a Little Less" Philosophy (14:14) Sponsors: Planful | Metaview (17:14) Avoiding People Leader Burnout (19:20) Building Your Peer Network (21:10) Tactical Work vs. Strategic Leadership (22:20) 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

    23 min
  2. Character AI's Annie Wickman on PMF, Google's Deal, and Humu

    6D AGO

    Character AI's Annie Wickman on PMF, Google's Deal, and Humu

    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

    43 min
  3. Startup Ethics: All In or Out

    APR 15

    Startup Ethics: All In or Out

    In this week's 'Dear Heretics' segment, Kelli and Nolan discuss a listener's dilemma about working with ethically questionable founders. They explore the tension between startup rule-bending culture and personal values, advising that leadership requires either full alignment with founders or graceful departure. They reflect on the impossibility of compartmentalizing personal trauma, the importance of workplace support networks, and practical advice for both those experiencing crises and colleagues supporting them. *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 NOLAN + KELLI ON LINKEDIN Nolan: https://www.linkedin.com/in/nolan-church/ Kelli: https://www.linkedin.com/in/kellidragovich/ — TIMESTAMPS: (00:13) Intro (00:52) Listener's Moral Dilemma with CEO (02:46) The Gamble With Me Philosophy (03:07) All In or All Out Leadership (04:09) Separating Morality from Alignment (04:38) The Danger of Staying When Misaligned (06:25) Toxic Without Knowing It (08:06) Modern Approach to Leadership Exits (08:53) Sponsors: Planful | Metaview (11:48) Is This Normal Startup Life? (12:07) Understanding Startup Rule-Bending (14:00) The Entrepreneurial Mindset (15:12) The Popsicle Stand Example (16:46) Building Your Leadership Brand (17:27) Working With vs Around Founders (18:19) The Lemonade Stand Rule (19:36) 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

    20 min
  4. VC Brett Queener Unpacks AI-Native Startups and the End of Grunt Work

    APR 10

    VC Brett Queener Unpacks AI-Native Startups and the End of Grunt Work

    HR Heretics welcomes back guest Brett Queener, Managing Director at Bonfire Ventures, for a check in on the current venture landscape. Fresh from raising a $245 million fund, Queener explores how AI is fundamentally changing software companies, emphasizing the need for rapid iteration and questioning traditional playbooks. He shares thoughtful perspectives on evaluating AI startups beyond the hype, the changing nature of talent requirements, and why successful companies must embrace a "change economy" mentality to thrive. *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 BRETT, NOLAN + KELLI ON LINKEDIN Brett: https://www.linkedin.com/in/brettqueener/ Nolan: https://www.linkedin.com/in/nolan-church/ Kelli: https://www.linkedin.com/in/kellidragovich/ — LINKS: Bonfire Ventures: https://www.bonfirevc.com/ — OTHER RECOMMENDED LINKS: The Change Economy: — TIMESTAMPS: (00:00) Intro (01:07) Bonfire's $245M New Fund (03:24) Today's Frothy AI Market (06:30) The 11X AI SDR Case Study (08:18) AI's Revolutionary Impact on Products (11:12) First-Time vs. Repeat Founders in AI (14:39) Sponsors: Planful | Metaview (17:38) Rethinking How Companies Operate (19:43) Hiring in the AI Era (22:58) Teams Getting Younger and AI Native (25:04) The Future of Junior Roles (28:22) The 11X Controversy Explained (30:29) Evaluating What's Real in AI Companies (33:29) Vibey Revenue and Real Value (37:00) Product Viability and Renewals (39:42) Assessing Founders and Products (42:10) The Case for In-Office Collaboration (44:31) The "Holy S**t" Product Moment (46:09) 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

    46 min
  5. APR 8

    Claude's Human-Like AI & Groundbreaking Research from Anthropic with Siadhal Magos

    In this installment of AI Corner, Siadhal Magos, Metaview CEO, and Nolan Church dissect Anthropic's groundbreaking paper “Tracing the thoughts of a large language model” released on March 27, 2025. They explore surprising findings: LLMs plan ahead rather than simply predicting next tokens, think across multiple languages simultaneously, and often present explanations that satisfy humans rather than reflecting their actual reasoning processes. The conversation highlights the paradox of developing powerful AI systems without understanding their workings, raising implications for deployment, safety, and the "intelligence on tap" paradigm reshaping our technological relationship. We should all be paying attention. 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 SIADHAL, NOLAN + KELLI ON LINKEDIN Siadhal: https://www.linkedin.com/in/siadhal/ Nolan: https://www.linkedin.com/in/nolan-church/ Kelli: https://www.linkedin.com/in/kellidragovich/ — LINKS: Anthropic’s featured paper: https://www.anthropic.com/news/tracing-thoughts-language-model Metaview: https://www.metaview.ai/ — OTHER RECOMMENDED LINKS: Mercor: https://mercor.com/ — TIMESTAMPS (00:13) Intro (00:45) Anthropic's Mind-Blowing Paper (01:37) LLMs Think Across Languages (02:04) Faked Reasoning in AI Models (02:28) AI Hallucinations Explained (03:00) First Paragraph Reveals Uncertainty (05:18) Beyond Next Token Prediction (07:23) Evaluating LLMs Without Understanding (08:44) More Human Than Software (10:05) Why You Should Experiment With AI (11:13) The Airplane Analogy (12:26) Safety Concerns for Future AI (12:54) Sponsors: Planful | Metaview (16:27) Dario Amodei on AI Self-Policing (18:05) OpenAI's $300B Valuation (19:33) Intelligence on Tap (22:02) Retraining Google Habits (24:35) Agentic AI & Reinforcement Learning (27:15) Human Training for AI Models (30:25) 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

    31 min
  6. APR 4

    Solving for False Negatives in Hiring with Arthur Matuszewski

    Today we're excited to introduce you to an episode of 10x Recruiting, a podcast from Metaview hosted by our very own Nolan Church. 10x Recruiting is focused on conversations with top talent leaders to help listeners build world-class teams and stay ahead in the evolving recruiting landscape. Today's guest is Arthur Matuszewski, who shares insights from his diverse career at Bridgewater, Better.com, and his firm Carrara. He emphasizes intellectual honesty, focusing on work outputs rather than titles, and avoiding false negatives in hiring. Nolan says he's one of the most insightful guests ever. Matuszewski advocates for evaluating talent based on actual value creation rather than pedigree, and stresses the importance of adapting recruitment strategies to each org's unique context rather than relying on standardized playbooks. Head to The 10x Recruiting Podcast on YouTube, Apple, or Spotify for more interviews like this one. YouTube: https://www.youtube.com/@10x_Recruiting_pod Apple: Spotify: — LINKS: Arthur’s LinkedIn: https://www.linkedin.com/in/arthurmatuszewski/ Carrara: https://www.carrara.is/ — TIMESTAMPS: (00:00) Intro (00:53) Episode preview (05:51) Arthur's career journey overview (07:53) Lessons learned at Bridgewater (10:41) Recruiting for teams vs individuals (12:35) Bridgewater's culture of experimentation (16:47) High attrition rate and false negatives (23:22) Better.com's rise and viral moment (28:02) Defining intellectual honesty (30:08) Carrara and focusing on the work (37:56) Balancing productivity with thinking time (40:03) Avoiding sunk costs in talent decisions (43:31) Carrara's process for delivering winners (45:43) Showing founders what the market is saying (47:19) Internal vs external talent perspectives (51:58) 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

    52 min
  7. APR 3

    Rethinking the HRBP Role with Lucy Adams, Disruptive HR

    In this episode, Kelli Dragovich and Nolan Church are joined by Lucy Adams, founder of Disruptive HR. Adams critiques traditional HR's rigid policies, advocating instead for judgment-based approaches that treat employees as grown-ups. The conversation explores challenges facing HR business partners, the evolution of DEI initiatives, and how organizations can create environments where people thrive through high-trust cultures, rather than compliance-driven systems. *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: Thatch makes it easy to give your team great healthcare. Save ~$1620 per employee yearly while giving them customizable plans. Visit https://thatch.AI/HR for a demo and receive a $100 gift card. 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 LUCY, NOLAN + KELLI ON LINKEDIN Lucy: https://www.linkedin.com/in/lucykadams/ Nolan: https://www.linkedin.com/in/nolan-church/ Kelli: https://www.linkedin.com/in/kellidragovich/ — LINKS: Disruptive HR: https://disruptivehr.com/ Lucy’s article “HR Business Partner: The toughest role in HR?”: https://disruptivehr.com/hr-business-partner-the-toughest-role-in-hr/ — TIMESTAMPS: (00:00) Intro (01:17) Lucy's Background and BBC Experience (03:08) Personal Connection and BBC Stories (04:25) Origins of Disruptive HR (07:00) Evolution of HR and Post-COVID Workplace Changes (11:39) Trust and Autonomy in Workplace Decisions (16:56) Trust as Foundation for Business Success (17:32) Sponsors: Thatch | Planful (20:27) Progressive HR Policies and Examples (23:53) HR Business Partner Role Challenges (25:13) Sponsor: Metaview (27:55) Messy Reality of Great HR Work (31:00) HR's Focus on Process vs. Real Impact (33:26) Current HR Trends and Community Concerns (35:56) DEI Evolution and Conversation Approaches (45:53) 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

    46 min
  8. APR 1

    Real Personal Crises at Work

    In this week's 'Dear Heretics' segment, Kelli and Nolan discuss the profound impact of personal crises on work life. They share vulnerable stories about caring for ill family members—Kelli's mother's recent stage four cancer diagnosis and Nolan's father-in-law's illness and passing. They reflect on the impossibility of compartmentalizing personal trauma, the importance of workplace support networks, and practical advice for both those experiencing crises and colleagues supporting them. *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: Thatch makes it easy to give your team great healthcare. Save ~$1620 per employee yearly while giving them customizable plans. Visit https://thatch.AI/HR for a demo and receive a $100 gift card. 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 NOLAN + KELLI ON LINKEDIN Nolan: https://www.linkedin.com/in/nolan-church/ Kelli: https://www.linkedin.com/in/kellidragovich/ — TIMESTAMPS: (00:00) Intro (02:24) Impact of Crisis on Professional Life (03:19) Becoming a Parent to Your Parent (03:41) The Adrenaline Phase vs. Reality Setting In (04:18) Nolan's Story of His Father-in-Law (05:47) How Crisis Changes Your Perspective (07:11) The Impossibility of Compartmentalizing Life (08:02) The Importance of Strong Work Relationships (09:21) The Speed of Life-Changing Events (10:01) Gaining Wisdom Through Difficulty (10:18) The Value of Having a Coach (12:22) Using Your Support System Effectively (13:19) Finding a New Balance in Crisis (14:10) Practical Ways to Help Someone in Crisis (14:49) Sponsors: Thatch | Planful (17:00) Navigating the Healthcare System (18:03) The Critical Need for Medical Advocacy (19:35) How Crisis Impacts Your Work Priorities (20:17) Asking the Right Questions When Supporting Others (21:04) Sponsor: Metaview 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

    23 min
4.9
out of 5
47 Ratings

About

After a decade+ of “blitz-scaling” companies, HR, talent, and People leaders now face an uncertain economy that has already seen big booms and busts. What will it take to construct the next generation of incredible businesses – and where can people leaders have the most business impact?     Hosts Nolan Church and Kelli Dragovich have been through it all, the highs and the lows – IPOs, layoffs, executive turnover, board meetings, culture changes, and more. With a lineup of industry vets and experts, Nolan and Kelli break down the nitty-gritty details, trade offs, and dynamics of constructing high performing companies. Through unfiltered conversations that can only happen between seasoned practitioners – Kelli and Nolan dive deep into the kind of leadership-level strategy that often happens behind closed doors. This show is for those who are ready to ditch conventional wisdom and figure out from first principles what works for their culture, business model, and industry, with the goal of building a resilient and enduring company. You’ll come away with real guidance for seeing around corners, building enduring companies, and carving out an impactful career – plus a newly-honed bullshit detector. Topics frequently touched on in this season include: building high performing cultures, compensation negotiation, performance reviews, company design, equity, M&As, recruiting the best talent, and how to manage your own psychology as a people leader. hrheretics.substack.com

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