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

Kelli and Nolan explore the art of professional boundary-setting and etiquette. After Nolan shared a LinkedIn post about declining a meeting with a founder who didn't show up on time to their scheduled call, the hosts examine the delicate balance between protecting one's time and extending grace to others. Their conversation delves into how personal boundaries, stress levels, and professional status influence our responses to professional missteps

*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/

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LINK TO NOLAN’S POST:

Community Regulation When People Break Social Etiquette

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TIMESTAMPS:

(00:00) Intro

(00:16) When LinkedIn Goes Nuclear: The Time Management Debate

(02:05) How Your Day Affects Your Tolerance

(04:14) Different Cultures, Different Rules: Looker vs Google Time Ethics

(07:48) Sponsors: Planful | Metaview

(10:48) The Mother Test: When Accountability Matters Most

(11:21) Calendar Hijacking: When Professional Boundaries Get Crossed

(13:08) Societal Rot or Personal Standards? The Unwritten Rules Debate

(15:34) Finding Your Boundary Line

(16:14) What's Your Unwritten Rule?

(16:22) Wrap

In this episode of HR Heretics, Nolan Church and Kelli Dragovich interview Jared Kleinert, founder of Offsite.com, who shares insights on planning effective team retreats that transform from "nice-to-have" into strategic "must-have" events for remote and hybrid companies. Kleinert emphasizes that successful offsites require intentional planning with clear objectives, arguing that thoughtfully designed retreats drive organizational alignment, build trust between teammates, and provide measurable business value beyond just logistics.

*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 JARED, NOLAN + KELLI ON LINKEDIN

Jared: https://www.linkedin.com/in/jaredkleinert

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

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

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LINK/S:

Offsite: https://marketplace.offsite.com/inquiry?utm=hrheretics

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TIMESTAMPS:

(00:00) Intro

(00:47) Offsite's Business Model and Vision

(02:17) Remote Work Trends and Offsite Planning

(04:49) Elements of a Successful Offsite

(09:38) Measuring Offsite ROI and Effectiveness

(14:00) Adapting Offsites During Economic Downturns

(16:26) Sponsors Planful | Metaview

(19:52) Strategic Offsite Planning and Best Practices

(26:46) Balancing Team Building and Business Performance

(30:34) Executive Offsite Tactics and Trust Building

(34:04) Pre-Offsite Preparation and Intention Setting

(37:15) Wrap

In this candid "HR Heretics" segment, Nolan and Kelli expose the hidden risks of equity compensation, including Nolan's $8 million DoorDash missed opportunity. They reveal essential questions about share counts, strike prices, and exercise windows that can make or break startup wealth. Their message: equity details are negotiable, but education is your responsibility—not the company's.

*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/

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TIMESTAMPS:

(00:13) Intro

(00:52) Being Smart about Equity

(01:46) Nolan's $8 Million Mistake

(03:05) Understanding Share Count

(04:44) Strike Price Explained

(06:00) Preferred Price vs. Strike Price

(07:43) Net Value Calculation

(08:42) Golden Handcuffs Reality

(10:31) Exercise Windows

(12:00) Negotiation Opportunities

(12:26) Tax Implications

(14:07) Early Exercise Benefits

(15:09) Sponsors: Planful | Metaview

(18:09) Additional Negotiation Tactics

(19:57) Executive Liquidity Options

(21:32) Double Trigger Provisions

(23:12) Vesting Schedule Negotiation

(24:00) Key Takeaways

(24:37) Personal Responsibility

(26:08) Resources & Research

(27:01) Final Thoughts

(27:23) Wrap

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: [email protected]

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 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/

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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

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: [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/

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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

In this episode, Nolan Church and Kelli Dragovich interview Troy Sultan who shares his journey from Google to founding Guide, an AI-powered recruiting coordination platform. Sultan challenges traditional recruiting assumptions, arguing modern candidates prefer transparency, speed, and self-service options that let them control their hiring experience.

*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 TROY, NOLAN + KELLI ON LINKEDIN

Troy: https://www.linkedin.com/in/troysultan/

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

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

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LINKS

Guide: https://www.guide.co/

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TIMESTAMPS:

(00:00) Intro

(01:10) Troy's Exit from Google

(01:44) The Cookie-Based Sales Strategy

(02:54) Resource vs. Gem

(03:33) Product vs. Go-to-Market Lessons

(05:23) Selling to Gem

(07:31) The Acquisition Strategy

(09:25) Working with Brokers

(11:46) Marketing to HR Leaders

(14:05) Sponsor: Planful | Metaview

(17:05) The Value of Candidate Experience

(19:42) Company Priorities vs. Actions

(22:20) Guide: AI-Powered Recruiting Coordination

(24:35) AI Adoption Challenges

(26:18) Authors vs. Editors Framework

(27:44) How Aria Works

(30:18) World-Class Candidate Experience

(31:31) The Self-Service Revolution

(34:03) Customer Industries and Use Cases

(37:20) Human Experience Across Job Types

(40:03) The Cultural Shift to Self-Service

(42:47) Wrap

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: [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

(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

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: [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 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/

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LINK/S:

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

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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

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: [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/

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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

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: [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 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/

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LINKS:

Bonfire Ventures: https://www.bonfirevc.com/

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OTHER RECOMMENDED LINKS:

The Change Economy:

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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