“HR Heretics” | How CPOs, CHROs, Founders, and Boards Build High Performing Companies
HR Heretics
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
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
Episodes
Mentioned books
May 8, 2025 • 39min
Creating the 'Airbnb for Offsites': Jared Kleinert on Building the Future of Work Retreats
Jared Kleinert, founder of Offsite.com, specializes in planning transformative team retreats for remote and hybrid teams. He highlights how strategic offsites elevate organizational alignment and build trust among team members. Kleinert shares insights on the shift towards meaningful retreats post-pandemic, emphasizing their role in enhancing company culture and engagement. He also discusses the importance of intentional planning to ensure these gatherings provide measurable business value and foster team cohesion.
20 snips
May 6, 2025 • 28min
The $8M DoorDash Mistake: Equity Offers
Nolan and Kelli unveil the hidden risks of equity compensation, sharing tales like Nolan’s missed $8 million opportunity with DoorDash. They emphasize that understanding share counts and strike prices is crucial for maximizing startup wealth. With practical advice, they equip listeners to navigate the complexities of equity offers and negotiate job terms effectively. The conversation also introduces innovative tools enhancing workforce management, underlining the need for self-education in the intricate world of equity grants.
8 snips
May 1, 2025 • 18min
Tobi Lütke Wants Shopify Employees to Use AI Reflexively — Should You? with Siadhal Magos of Metaview
In this installment of AI Corner, Siadhal Magos, the CEO of Metaview, and Nolan Church explore the emerging trend of "CEO AI mandates" from the likes of Tobias Lütke and Aaron Levie at Box.*Email us your questions or topics for Kelli & Nolan: hrheretics@turpentine.coFor 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/hereticsKEEP UP WITH SIADHAL, NOLAN + KELLI ON LINKEDINSiadhal: https://www.linkedin.com/in/siadhalNolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—TIMESTAMPS:(00:00) Intro(00:33) The CEO AI Mandate Trend(01:22) Siadhal's Take on AI Mandates(02:35) AI Orchestration as a Career Necessity(03:00) Headcount Management in the AI Era(04:04) AI Leverage vs. Team Size(06:03) Sponsors: Thatch | Planful(08:13) AI Upskilling and Education(09:21) Personal AI Tuition in Organizations(10:18) The Reflexive AI Problem-Solving Approach(11:27) Show and Tell: Learning from Power Users(12:00) Knowing What's Possible as Motivation(13:22) Carrot vs. Stick: Recognizing AI Adoption(14:38) Beyond AI as a Metric: Performance is the Goal(15:34) Wrap(15:58) 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
Apr 29, 2025 • 19min
360 Reviews Without the Dread
In this week's 'Dear Heretics' segment, Kelli and Nolan unpacks the intricacies of 360 reviews from a management perspective, offering pragmatic approaches to synthesizing overwhelming feedback data. They contrast methodical theme-based analysis with modern AI-assisted solutions, emphasizing that meaningful feedback isn't an annual crucible but a continuous conversation peppered with five compliments per criticism.*Email us your questions or topics for Kelli & Nolan: hrheretics@turpentine.coFor 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/hereticsKEEP UP WITH NOLAN + KELLI ON LINKEDINNolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—TIMESTAMPS:(00:00) Intro (00:36) Dear Heretics - 360 Reviews Question (00:52) Good vs Bad 360 Reviews (06:34) Sponsors - Planful | Metaview (09:34) Using AI for 360 Reviews (11:38) On Using AI Tools (13:27) Sports Analogy Break (14:45) Getting the Ball Rolling (15:22) Continuous Feedback Approach (17:21) 5:1 Positive Ratio (17:59) Explaining the Why in Feedback (19:20) Making Feedback Enjoyable (19:26) 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
10 snips
Apr 25, 2025 • 43min
Troy Sultan: How Guide Turned RCs into Iron Man
Troy Sultan, CEO and founder of Guide, shares his journey from Google to revolutionizing recruitment with AI. He tackles the outdated assumptions of traditional hiring, advocating for speed and transparency. Sultan discusses the importance of empowering candidates with self-service options, transforming their experience. He also emphasizes the cultural shift towards automation in hiring processes and the need for HR leaders to adapt. With insights on improving candidate experiences, Troy invites a rethinking of power dynamics in recruitment.
6 snips
Apr 22, 2025 • 23min
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.coFor 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/hereticsKEEP UP WITH NOLAN + KELLI ON LINKEDINNolan: 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
5 snips
Apr 17, 2025 • 43min
Character AI's Annie Wickman on PMF, Google's Deal, and Humu
Annie Wickman, Head of People at Character AI and former Googler, shares her unique journey from being the first non-founder at Humu to leading talent strategies at Character AI. She discusses the essential balance between product-market fit and company culture, and how this interplay affects internal dynamics. Annie also dives into her experiences with Google’s strategic deals and offers insights into rebuilding organizational trust. Additionally, she touches on the emotional challenges of leadership in venture capital and maintaining a strong team culture during transitions.
7 snips
Apr 15, 2025 • 20min
Startup Ethics: All In or Out
Explore the ethical tightrope that startups walk, where personal values clash with innovative ambition. Hear advice on whether to align with ethically questionable founders or gracefully step away. Delve into the importance of integrity in leadership and the signs of workplace toxicity. Discover insights on building supportive networks amid personal crises. Plus, learn about innovative tools that enhance workforce management, like AI-powered solutions that revolutionize recruitment processes.
Apr 10, 2025 • 46min
VC Brett Queener Unpacks AI-Native Startups and the End of Grunt Work
Brett Queener, Managing Director at Bonfire Ventures, shares insights on the evolving venture landscape and the impact of AI on software startups. He dives into the challenges of evaluating AI startups amidst the hype and stresses the importance of rapid adaptation. Queener highlights how AI is revolutionizing recruitment, making processes more efficient with tools like MetaView. He also discusses the changing nature of talent needs and the necessity for companies to embrace a mentality of continuous change in today's competitive market.
13 snips
Apr 8, 2025 • 31min
Claude's Human-Like AI & Groundbreaking Research from Anthropic with Siadhal Magos
Siadhal Magos, CEO of Metaview and an AI pioneer, joins to explore Anthropic's landmark findings on large language models. They discuss how AI doesn't just predict but can plan ahead and process multiple languages at once. The conversation delves into the paradox of powerful AI systems operating without full comprehension of their reasoning, raising safety concerns. Siadhal highlights the crucial role of human collaboration in refining AI through data annotation, shaping the way forward in hiring and technology’s impact on our work.
