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

For today's essential Heretics 101 feature, Kelli and Nolan do a deep dive into executive recruiting mastery with VC Andy Price, covering why exec hires fail, back-channeling strategies, post-hire support, and building scalable leadership teams.

*Email us your questions or topics for Kelli & Nolan: [email protected]

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 platform built for recruiting. Our suite of AI agents work across your hiring process to save time, boost decision quality, and elevate the candidate experience.

Learn why team builders at 3,000+ cutting-edge companies like Brex, Deel, and Quora can’t live without Metaview.

It only takes minutes to get up and running. Check it out!

KEEP UP WITH ANDY, NOLAN + KELLI ON LINKEDIN

Andy: https://www.linkedin.com/in/andyprice1/

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

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

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TIMESTAMPS:

(00:00) Intro

(01:02) Why Executive Hit Rates Are So Low

(04:01) The Artisanal Process: "Soaking" with Companies

(05:21) Back-Channeling Strategy

(07:11) Recruiters Are Overpaid: The Real Work Happens After Hire

(08:24) When Not to Hire - Too Early Stage Warning Signs

(09:01) Sponsors: Planful & MetaView

(12:46) How to Vet Search Firms

(14:00) Experience vs. Trajectory

(16:17) Scaling Up and Comers

(17:30) Executive Career Management

(20:25) Executive Tenure: Why the "One Year BS" Doesn't Work

(22:36) The Authenticity Generation

(23:52) Wrap

Nolan and Kelli dive deep into the viral Astronomer scandal where the CEO and Chief People Officer were exposed having an affair during a Coldplay concert kiss cam moment. They examine the hypocrisy of executive leadership, the responsibilities that come with high-profile roles, and how this incident damages trust in HR leadership across the industry.

*Email us your questions or topics for Kelli & Nolan: [email protected]

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 platform built for recruiting. Our suite of AI agents work across your hiring process to save time, boost decision quality, and elevate the candidate experience.

Learn why team builders at 3,000+ cutting-edge companies like Brex, Deel, and Quora can’t live without Metaview.

It only takes minutes to get up and running. Check it out!

KEEP UP WITH NOLAN + KELLI ON LINKEDIN

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

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

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TIMESTAMPS:

(00:00) Intro

(00:13) Opening & Context

(01:51) Initial Reactions

(05:11) The Hypocrisy Factor

(08:23) Leadership Responsibility

(10:00) Work-Life Integration

(15:58) Modern Visibility

(18:00) Hypothetical Solutions

(21:26) The Gwyneth Paltrow Response

(25:00) Impact on Employees

(26:00) Industry Implications

(30:14) Wrap

In this episode of HR Heretics, Kelli and Nolan sit down with Sarah Tilley, SVP of Global Talent at ServiceNow, to unpack how a $199B company is revolutionizing talent acquisition with AI. Sarah breaks down their two-speed transformation strategy—from optimizing basic recruiting processes to unlocking game-changing talent market intelligence that most companies can't even imagine yet.

*Email us your questions or topics for Kelli & Nolan: [email protected]

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 platform built for recruiting. Our suite of AI agents work across your hiring process to save time, boost decision quality, and elevate the candidate experience.

Learn why team builders at 3,000+ cutting-edge companies like Brex, Deel, and Quora can’t live without Metaview.

It only takes minutes to get up and running. Check it out!

KEEP UP WITH SARAH, NOLAN + KELLI ON LINKEDIN

Sarah: https://www.linkedin.com/in/sarahtilley/

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

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

—

ServiceNow: https://www.servicenow.com/

—

TIMESTAMPS:

(00:00) Intro

(01:09) What is ServiceNow?

(04:22) The Two-Speed AI Strategy

(13:08) Getting Started with AI Transformation

(20:11) The Self-Service Recruiting Era

(25:02) The Low Hire, Low Fire Market

(28:00) Tracking AI Adoption

(32:29) Quality of Hire Deep Dive

(35:43) The Future: Skills-Based Hiring

For today's essential Heretics 101 feature, Kelli and Nolan talk to Ethena CPO Melanie Naranjo, challenging empathy-driven management, exposes toxic executive dynamics, and advocates for logic over emotion in workplace leadership.

*Email us your questions or topics for Kelli & Nolan: [email protected]

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 platform built for recruiting. Our suite of AI agents work across your hiring process to save time, boost decision quality, and elevate the candidate experience.

Learn why team builders at 3,000+ cutting-edge companies like Brex, Deel, and Quora can’t live without Metaview.

It only takes minutes to get up and running. Check it out!

KEEP UP WITH MELANIE, NOLAN + KELLI ON LINKEDIN

Melanie: https://www.linkedin.com/in/melanie-naranjo

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

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

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Ethena: https://www.goethena.com/

—

TIMESTAMPS:

(00:00) Intro

(00:44) CEO-CHRO Partnership Transformation

(02:23) The State of HR Leadership

(04:08) The HR Crisis Revealed

(05:20) The Root Cause Analysis

(06:58) Sponsors: Planful | Metaview

(10:00) The Anti-Empathy Argument

(12:45) HR Community Dysfunction

(14:21) The Gender Dynamics Truth

(15:28) Executive Team Toxicity Exposed

(17:13) The Politics Behind Dysfunction

(19:39) Beyond Meritocracy

(21:00) The Three Questions Framework

(21:54) The Anti-PIP Philosophy

(24:00) Direct Feedback That Works

(24:42) Wrap

For today's essential Heretics 101 feature, Kelli and Nolan explore compensation testing, remote culture scaling, leadership transparency, and AI adoption challenges through the analytical lens of Christine Centa, HashiCorp's Chief People Officer.

*Email us your questions or topics for Kelli & Nolan: [email protected]

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 platform built for recruiting. Our suite of AI agents work across your hiring process to save time, boost decision quality, and elevate the candidate experience.

Learn why team builders at 3,000+ cutting-edge companies like Brex, Deel, and Quora can’t live without Metaview.

It only takes minutes to get up and running. Check it out!

KEEP UP WITH PETER, NOLAN + KELLI ON LINKEDIN

Christine: https://www.linkedin.com/in/christine-centa-0a809b7/

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

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

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HashiCorp: https://www.hashicorp.com/en

—

TIMESTAMPS:

(00:00) Introduction & Christine's Background

(01:15) The Compensation Specialist to CPO Transition

(02:26) Current Compensation Landscape & Market Data

(04:00) The Midpoint Experiment

(05:28) Equity Strategy & New Grant Structures

(06:20) Going Public: Private to Public Transition

(07:28) Sponsor: Planful | MetaView

(10:27) Remote Work Philosophy & Scaling Challenges

(11:53) The Connection Crisis

(13:00) Leadership Dynamics: The Professor & Accountant

(13:51) Transparency as Strategy

(14:40) AI Strategy & Implementation Reality

(16:00) AI in Recruiting: The Future Frontier

(17:17) The AI Arms Race

(18:00) The Work Behind the AI Dream

(19:25) Preparing Teams for AI Future

(20:09) Wrap

Emergency pod: Returning guest Peter Walker (Carta's Head of Insights) analyze the controversial Windsurf deal, where Google's acqui-hire left non-founder employees without equity payout. They unpack the deal, reference Character AI's precedent, and explore how AI-era deals increasingly prioritize top researchers over broader employee bases, fundamentally changing startup risk calculations

*Email us your questions or topics for Kelli & Nolan: [email protected]

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 platform built for recruiting. Our suite of AI agents work across your hiring process to save time, boost decision quality, and elevate the candidate experience.

Learn why team builders at 3,000+ cutting-edge companies like Brex, Deel, and Quora can’t live without Metaview.

It only takes minutes to get up and running. Check it out!

KEEP UP WITH PETER, NOLAN + KELLI ON LINKEDIN

Peter: https://www.linkedin.com/in/peterjameswalker/

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

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

—

RELATED LINKS:

Windsurf’s CEO goes to Google; OpenAI’s acquisition falls apart

https://techcrunch.com/2025/07/14/cognition-maker-of-the-ai-coding-agent-devin-acquires-windsurf/

Carta:

https://carta.com/

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TIMESTAMPS:

(00:00) Intro

(00:52) Breaking News: The Windsurf Situation

(01:12) The OpenAI-Microsoft IP Rights Drama

(03:01) Plot Twist: Cognition's Counter-Offer

(04:49) The Employee Equity Problem

(06:00) Defending Against "That's How Deals Work" Critics

(08:00) The Scarlet Letter Effect

(10:00) Regulatory Background: The Lina Khan Era

(12:00) Revealed Behavior: What This Shows About Values

(13:25) Sponsors: Planful | Metaview

(17:00) Talent vs. Product Separation

(19:53) The AI Era's R&D Researcher Obsession

(22:00) Unequal Distribution of Outcomes

(23:28) What Comes Next: Evaluating Startup Risk

(24:00) The Founder Psychology Bet

(25:00) Equity Structure Solutions

(28:58) Becoming AI Native: Personal Brand Strategy

(30:56) The New Reality: Expecting Less Care

For today's essential Heretics 101 feature, Kelli and Nolan examine the persistent challenge of HR professionals becoming genuine business leaders. Jeff Diana Investor/Entrepreneur, and former CPO of Calendly, join in to dissect tactical strategies for developing business acumen, moving beyond traditional people operations to drive meaningful organizational impact through financial literacy and strategic thinking.

*Email us your questions or topics for Kelli & Nolan: [email protected]

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 JEFF, NOLAN + KELLI ON LINKEDIN

Jeff: https://www.linkedin.com/in/jeff-diana-a1906212/

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

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

—

TIMESTAMPS:

(00:00) Intro

(01:21) The Frustration: Why "HR at the Table" Still Doesn't Work

(02:13) Jeff's Do's and Don'ts Framework for Business Leadership

(04:26) KD's C-Suite Litmus Test

(05:50) The Controversial Take: Understanding Founder Irrationality

(06:49) Jeff's "Layers of the Cake" Business Metrics

(08:35) Sponsors: Planful | MetaView

(11:35) Synthesizing Learning for Your Team

(12:14) Being the Best-Run Function Strategy

(13:43) Career Mobility Benefits

(14:10) The SuccessFactors Sales Kickoff Story

(15:33) Wrap

Kelli and Nolan critically examine Bolt CEO and Founder Ryan Breslow's announcement that they eliminated their HR department in favor of "People Ops", questioning whether this rebranding actually improves efficiency or just represents clickbait without meaningful organizational change. They explore the tension between removing perceived bureaucratic middlemen and maintaining necessary workplace oversight.

*Email us your questions or topics for Kelli & Nolan: [email protected]

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/

—

Related Links:

Ryan Breslow’s LinkedIn Post:

https://www.linkedin.com/posts/ryanbreslow_bolt-has-eliminated-its-hr-department-activity-7340377688517365761-0TcL/

—

TIMESTAMPS:

(00:00) Intro

(00:13) Bolt's HR "Elimination" Announcement

(01:11) You Gotta Understand the Source First

(02:43) Way to Say Something Without Really Saying Anything

(03:24) Discussion: Good HR vs. Bad HR and Over-Planning

(04:37) Why HR Gets Targeted: Speed and Headcount Issues

(05:36) Who is People Ops Really?

(06:21) Sponsors: Planful | Metaview

(09:21) Who is People Ops Really? (continued)

(10:07) Business Risk and Future of HR Functions

(11:01) The Shift Has Already Been Happening

(11:58) The Work Doesn't Go Away

(12:22) Future of Work: AI Coaching and Managing Agents

(13:21) Wrap

A few weeks ago, we started bringing back essential Heretics 101 content. Today we're revealing insider secrets of equity negotiation that could save you millions. Colleen McCreary recommended this episode, and the stakes couldn't be higher.

*Email us your questions or topics for Kelli & Nolan: [email protected]

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

(00:32) The Problem (HR Leaders Don't Understand Equity)

(02:05) The Four Essential Questions Checklist

(02:14) Question #1 (What's the Fully Diluted Share Count?)

(03:53) Question #2 (What's the Strike Price/409A Valuation?)

(05:03) Question #3 (What's the Last Preferred Price?)

(07:51) The Golden Handcuffs Reality Check

(09:38) Question #4 (What's Your Exercise Window?)

(10:51) The Negotiation Secrets They Don't Tell You

(12:08) Why Strike Price Appreciation Kills You

(13:55) Sponsors: Planful | Metaview

(16:44) Advanced Negotiation Tactics

(21:51) Don't Take Equity at Face Value

(22:47) Your Responsibility To Do the Research

Today's episode examines friend of the pod/recurring guest Colleen McCreary's "CEO-VP of HR divorce rate" concept, sparked by a VC's call about his CEO's failed six-month relationship with a seasoned HR leader. Colleen, Kelli, and Nolan explore why traditional interviews miss critical compatibility issues, the tendency to let conflicts fester rather than address them early, and essential strategies for either salvaging these crucial partnerships or ending them professionally.

*Email us your questions or topics for Kelli & Nolan: [email protected]

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 COLLEEN, NOLAN + KELLI ON LINKEDIN

Colleen: https://www.linkedin.com/in/colleenmccrearychiefpplofficer/

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

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

—

LINKS:

Colleen’s Medium article on Founder CEO & Head of HR Divorce Rates:

https://medium.com/@colleenwheelermccreary/founder-ceo-head-of-hr-divorce-rates-c233c7fda7dc

TIMESTAMPS:

(00:00) Intro

(00:28) The CEO-VP of HR Divorce Rate Post Origin Story

(03:34) Learning from LJ Brock & Brian Armstrong's Relationship

(04:13) What Interview Processes Miss: The Hard Stuff

(06:13) Colleen's Trigger: Counter-Offers as Extortion

(07:39) Why HR Leaders Need to Figure Things Out

(08:51) Asking About Traumas in the Interview Process

(09:32) Expecting Turbulence vs. Throwing in the Towel

(10:14) Sponsors: Planful and Metaview

(13:14) The Festering Problem: Avoiding vs. Addressing Issues

(16:05) Molehills vs. Mountains: Managing Founder Relationships

(18:06) Being a Filter, Not a Burden

(18:43) The LinkedIn Marriage Analogy

(20:35) Agency & Experience: First-Time Leaders vs. Veterans

(21:39) Earning the Right & Paying Your Dues

(23:52) Staying Misaligned: A Conscious Choice

(25:19) Amicable Divorces & Doing It Right

(26:10) Taking the High Road: Long-term Relationship Impact

(27:10) 30-Year Relationships Still Matter

(28:05) Wrap