Iain Roberts, Global Head of Employee Experience at Airbnb, discusses experimenting in HR in 2025, the design-thinking reshaping organizational structures, and why CEO Brian Chesky’s ‘Founder Mode’ is much misinterpreted. Iain covers innovative approach to flexible work, cross-functional alignment, and treating employee programs as evolving products requiring continuous refinement.

*Email us your ‘Dear Heretics’ questions: [email protected]

**For coaching and advising inquire at

https://kellidragovich.com/

HR Heretics is a podcast from Turpentine.

—

Support HR Heretics Sponsor: 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

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LINK/S:

Airbnb: https://www.airbnb.com/

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REFERENCE/S:

NVIDIA’s Jensen Huang says that IT will ‘become the HR of AI agents’:

https://fortune.com/2025/01/09/nvidia-ceo-jensen-huangt-take-over-hr-ai-agents/

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KEEP UP WITH IAIN, NOLAN + KELLI ON LINKEDIN

Iain: https://www.linkedin.com/in/robertsiain/

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

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TIMESTAMPS:

(00:00) Intro

(00:13) From Designer to HR Leader: Iain's Journey

(01:15) "Everything Needs to Be Designed" Philosophy

(03:09) Designing Systems of People and Structures

(04:47) Bringing Design Thinking to HR at Airbnb

(08:03) Airbnb's One Roadmap Approach: 7,000 People, One Focus

(07:21) Top-Down vs. Bottom-Up Culture & Innovation

(10:26) Tactically Transforming an HR Team with Design Thinking

(11:47) Treating HR as Products and Services

(13:14) The Future of HR Product Management

(14:36) Sponsor: Metaview

(16:30) Founder Mode: Misinterpretations and Brian Chesky's Approach

(23:00) Airbnb's Shift to a Single Product Roadmap

(26:54) Design-Led Culture and Attention to Detail at Airbnb

(28:48) Prototyping & Iterating with Human Experiences: Challenges

(30:50) Airbnb's Gathering Strategy and Flexible Work Philosophy

(33:48) Airbnb's Contrarian Stance on Remote Work (Live & Work Anywhere)

(39:45) Wrap

Anna Binder, Head of People at Asana, shares her journey as an HR leader, her approach to board membership at CultureAmp, and her philosophy on talent management. The discussion covers the nitty gritty of preparing and contributing in board meetings, long-term DEI initiatives, and the importance of authentic leadership in HR, particularly highlighting the value of playing the long game in organizational development.

*Email us your ‘Dear Heretics’ questions: [email protected]

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

HR Heretics is a podcast from Turpentine.

—

Support HR Heretics Sponsor: 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

—

LINK/S:

Asana: https://asana.com/

—

KEEP UP WITH ANNA, NOLAN + KELLI ON LINKEDIN

Anna: https://www.linkedin.com/in/annabinder/

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

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TIMESTAMPS:

(00:00) Intro(01:47) Becoming a Board Member at Culture Amp(05:33) The Importance of Taking Calls and Building Relationships(07:10) How to Prepare for and Participate Effectively on a Board(11:48) Examples of "Operating" vs. Asking the Right Questions as a Board Member(14:57) Sponsor: Metaview(16:57) Anna's Experience Building MuleSoft(19:00) Navigating Disagreements and Being "Invited to Exit"(21:12) Sharing the News and the Importance of Transparency(22:50) Finding the Right Fit and the Role of Values(25:57) Joining Asana(26:26) Ensuring Alignment During the Interview Process(29:35) How to Maintain Stamina and Interest Over a Long Tenure(31:14) Examples of Attention to Detail and Values Alignment at Asana(31:46) Examining the CEO's Calendar During Interviews(33:05) Anna's Controversial Recruiting Philosophy(33:16) Recruiting Top Talent(35:42) DEI at Asana: Long-Term Vision and Business Outcomes(39:38) The Importance of Being in the Right Room(40:09) Playing the Long Game on DEI(41:59) Encouraging People to Enter the Field(44:31) Outro

Nolan and Kelli talk about retaining top-performing employees (the crucial 1%) and emphasize that compensation alone isn't sufficient; leaders must combine verbal recognition, proactive compensation strategies, transparency, and genuine appreciation. They stress the importance of eliminating compensation anxiety for these key employees and building long-term relationships, and argue that thoughtful, personalized treatment of top talent ultimately benefits both the individual and organization.

Email us your ‘Dear Heretics’ questions: [email protected]

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

HR Heretics is a podcast from Turpentine.

—

Support HR Heretics Sponsor: 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) Introdu(00:13) Defining the Top 1%(00:57) Shifting Trends in Job Offers and Compensation(02:04) Appreciating Top Talent(03:01) The Importance of Appreciation Beyond Monetary Compensation(03:56) Balancing Appreciation and Competitive Compensation(05:02) Transparency in Compensation Decisions(07:49) Sponsor: Metaview(09:43) Four Pillars: Appreciation, Thoughtfulness, Proactivity, and Transparency(12:08) The Expectation of Transparency(12:43) Long-Term Career Involvement with Top Performers(14:21) Reciprocity in Employer-Employee Relationships(14:53) Wrap

Nolan and Kelli talk about AI's role in hiring processes, sparked by Anthropic's policy against using AI in job applications. They explore the tension between AI as a valuable tool and its potential for interview deception, ultimately advocating for a more integrated approach where candidates openly demonstrate their AI usage skills rather than attempting to restrict or hide it.

Email us your ‘Dear Heretics’ questions: [email protected]

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

HR Heretics is a podcast from Turpentine.

—

Support HR Heretics Sponsor: 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/

—

RECOMMENDATIONS FOR THIS PODCAST:

Gizmodo Article: “Anthropic Wants You to Use AI—Just Not to Apply for Its Jobs”

https://gizmodo.com/anthropic-wants-you-to-use-ai-just-not-to-apply-for-its-jobs-2000558490

Anthropic: https://www.anthropic.com/

Final Round AI: https://www.finalroundai.com/

Sora: https://openai.com/sora/

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TIMESTAMPS:

(00:00) Intro(01:26) Initial Reactions and Perspectives to Anthropic’s Policy(02:23) AI as a Tool vs. Replacement for Human Skills(03:36) AI-Powered Interview Cheating.(04:11) Practical AI Usage Throughout the Application Process(06:21) Sponsor: Metaview(08:15) Authenticity vs. AI Assistance(10:09) Polarities and Gradients of AI Usage(11:16) The Problem of Cheating and the "Open Book" Interview Approach(12:30) Using AI During In-Person Interviews(13:33) Adapting to AI in Hiring and Education(14:18) Audience Engagement and Future Solutions(15:03) Wrap

Entrepreneur Jesse Tinsley - founder of Employer.com and other successful tech ventures - discusses his consortium's bid to acquire TikTok alongside MrBeast. The dialogue with Kelli and Nolan examines the philosophical and practical implications of executive compensation reduction during corporate restructuring, while illustrating how digital discourse can evolve into substantive debate when moved from social media to direct dialogue.

*Email us your ‘Dear Heretics’ questions: [email protected]

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

HR Heretics is a podcast from Turpentine.

—

Support HR Heretics Sponsor: 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

—

LINK/S:

Employer.com: https://www.employer.com/

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KEEP UP WITH JESSE, NOLAN + KELLI ON LINKEDIN

Jesse: https://www.linkedin.com/in/jessetinsley

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

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

—

TIMESTAMPS:

(00:00) Intro(01:55) Update on the TikTok Acquisition(02:25) Motivation Behind Acquiring TikTok with Mr. Beast(04:38) How TikTok Fits into Jesse's Business Portfolio(07:07) Discussion on Executive Compensation and Layoffs(10:28) Specifics on Executive Salary Cuts(11:00) Sponsor: Metaview(12:57) Executive Compensation(15:34) The Importance of Leadership Accountability(18:16) Cultural Impact of Executive Pay Cuts(19:12) Wrap(21:05) Outro

Adam Ward (founding partner, Growth by Design) discusses the current landscape of executive hiring in people/talent roles, particularly the prevalence of "pocket listings" - positions filled through private networks rather than public postings. He offers insights into what CEOs value in people leaders (business-driven mindset, operational excellence), how candidates can effectively navigate professional networks, and the importance of structured hiring processes.

*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.

—

📰 Be notified early when Turpentine's drops new publication: https://www.turpentine.co/exclusiveaccess

Support HR Heretics Sponsor:

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

LINKS:

Growth By Talent: https://www.gbdtalent.com/

—

KEEP UP WITH ADAM, NOLAN + KELLI ON LINKEDIN

Adam: https://www.linkedin.com/in/adampward/

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

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

—

REFERENCE:

“Give and Take” by Adam Grant:

https://adamgrant.net/book/give-and-take/

—

TIMESTAMPS:

(00:00) Intro

(00:57) The "Pocket Listing" Phenomenon in Executive Hiring

(02:22) Unpacking the Reasons Behind Covert Hiring Practices

(03:59) Practical Strategies for Candidates to Expand Their Networks and Access Hidden Opportunities

(05:03) Cultivating a Personal "Board of Advisors" for Career Guidance and Opportunity Awareness

(08:41) The Importance of "Give and Take" in Networking and Building Mutually Beneficial Relationships

(09:43) Defining the Qualities of a Successful Head of People/Talent: The CEO's Perspective

(11:10) A "Business-Driven" Approach to HR Leadership

(13:04) Moving Beyond Quantity to Focus on Quality

(16:04) Sponsor: Metaview

(18:07) Identifying Must-Have Skills and Experiences for a Head of People Role

(19:14) The "CEO Whisperer" Role: Balancing Support and Independent Counsel

(21:57) Identifying Traits That May Hinder a People Leader's Job Search Success

(23:08) Addressing Polarities and Calibrating Expectations Within Hiring Teams

(26:48) The Resurgence of Candidate Experience as a Differentiator in a Competitive Market

(28:53) Why Top Talent Approaches Job Opportunities with Caution

(31:24) Defining the Scope and Focus of the Head of Talent Role in Today's Environment

(36:04) How Candidates Should Effectively Interact with Executive Search Firms

(41:52) Values Alignment: How To Find a Successful Values Match For Company Culture

(42:05) What Causes Executive Placements to Fail?

(44:55) Wrap

Kelli and Nolan examine the art of building authentic company values. Through real-world experiences, they reveal the methodical process of transforming abstract principles into tangible organizational behavior that drives meaningful cultural change.

*Email us your ‘Dear Heretics’ questions: [email protected]

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

HR Heretics is a podcast from Turpentine.

—Support HR Heretics Sponsor: 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(00:13) Discussion on Company Values(01:30) Importance of Leadership and Top Performer Alignment(02:19) Company Core Values and Honesty(02:43) Scaling Culture in Founder-Led Companies(03:46) Making the Intangible Tangible(04:23) Revealed vs. Stated Character(04:40) The Benefit of Outsourcing the Process of Developing Company Values(05:54) Company Values Are Always Evolving(06:27) The Goldilocks Approach(07:48) Sponsor: Metaview(09:52) Quick Process to Rough Draft(10:20) Doordash Example(11:56) Pendo's Working Committee and Bottoms Up Approach(13:19) The Importance of Timing(14:25) Wrap

Kelli and Nolan tackle a listener's frustration with a painfully slow reorg process, diving into the eternal tension between perfect planning and actually running the business. When HR and legal reviews stretch into week four, should you keep waiting for perfection or pull the trigger? Towards the end of the episode, Kelli and Nolan get into brass tacks offering tactical timelines to execute a reorg based on hypothetical examples.

*Email us your ‘Dear Heretics’ questions: [email protected]

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

HR Heretics is a podcast from Turpentine.

—Support HR Heretics Sponsor: 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

(00:19) The Reorg Dilemma

(00:56) Challenges in Big Companies

(03:00) Balancing Perfection and Speed

(04:43) HR & Legal Risk

(08:55) Sponsor: Metaview

(10:49) Employment Lawyers’ Limitations

(12:33) Intellectual Trap

(13:28) Workshopping Different Scenarios

(15:23) Wrap

Tom Clayton, COO of Peek, shares his unconventional playbook for building world-class teams. From his data-driven "employee attribute chart" to his rule of "don't be a brand b***h," Tom breaks down how he's scaled companies from 50 to 2000+ employees.

He dishes on everything from why he sends champagne to candidates' hotel rooms to why he encourages employees to quit and start their own companies.

If you’re listening on podcast platforms, be sure to check out our Substack or YouTube channel to see Tom’s framework slides onscreen:

Substack: https://hrheretics.substack.com/p/smart-hiring-with-tom-clayton

YouTube: Smart Hiring with Tom Clayton

*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.

—

📰 Be notified early when Turpentine's drops new publication: https://www.turpentine.co/exclusiveaccess

Support HR Heretics Sponsor:

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 LINK:

The Sales Acceleration Formula: Using Data, Technology, and Inbound Selling to go from $0 to $100 Million: https://www.amazon.com/Sales-Acceleration-Formula-Technology-Inbound/dp/1119047072

—

TIMESTAMPS:

(00:00) Intro(00:37) The Employee Attribute Chart Explained(03:41) Contextual Attributes(05:00) Answering with Cues vs. Direct Questions(10:46) Training Others on the Attribute Chart(11:28) The Value of Multiple Interviews(13:15) Emotional Investment in the Group(14:17) Speed Dating Analogy for Interviews(14:27) Sponsor: Metaview(16:21) Expediting the Interview Process(17:03) Job Simulations and Work Trials(18:36) Difficulties with Senior Exec Simulations(20:39) The Importance of the "Mock Exec Meeting"(21:57) Making Intangibles Tangible(22:54) Evolution of Team Building Attributes(23:09) Team Building and Outreach(26:47) Don't Be a "Brand B***h"(29:11) The Value of Personal Touches(32:31) Sustaining Great Teams During Hyperscale(35:00) Meta's Performance Process(38:39) Encouraging Entrepreneurship(42:23) Altruism in the Industry(42:31) Wrap

Kelli and Nolan unpack the delicate art of layering – that awkward moment when someone gets a new boss – while calling out the pitfalls of secret searches and celebrating the often-forgotten heroes of early startup days. Equal parts tactical advice and therapy session for growing companies.

*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.

—

📰 Be notified early when Turpentine's drops new publication: https://www.turpentine.co/exclusiveaccess

Support HR Heretics Sponsor:

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(00:13) Layering Question on Dear Heretics(02:06) Initial Thoughts on Layering(02:58) Human Aspect of Layering(03:43) Importance of Coaches & Advisors(04:00) New Hires vs Existing Employees(07:16) Confidential Search on Layering(10:08) Sponsor: Metaview(12:02) Handling Layering: CEO/CPO Perspective(14:13) Expanding Roles in Startups(16:00) New Executives and Fail States(16:57) The Shepherd Role of a Leader(17:18) The Layered Employee's Perspective(18:05) Two Paths: Spiteful vs. Gracious(20:18) Building Something Bigger Than Yourself(20:59) Maturity Matters(21:20) Wrap