Tony Castellanos has seen recruiting from every angle: Google, Square, various startups, and now as Head of Compensation & Talent at Nextdoor. In this episode, Tony breaks down how his team is using AI to rethink recruiter training, eliminating the "practice on candidates" problem by simulating real conversations with virtual personas. He and Rob also dive into community-led recruiting, why values...

André Martin has been CLO at Nike, Mars, and Target, so when he talks about the cost of disengagement, we listen. In this episode, André joins Rob to talk about his new book Wrong Fit, Right Fit, why work feels broken for so many, and what leaders can do about it. From rewriting job descriptions to rethinking culture as a daily operating system instead of a post...

Tracy Layney has led HR at iconic brands like Levi's, Old Navy, and Shutterfly, so it's no surprise she's now training the next generation of CHROs at the University of Chicago's Booth School of Business. Tracy joins Rob to unpack why HR's role is more complex (and powerful) than ever before, and how her coursework is helping senior people leaders develop the human capital strategies their companies desperately need. She breaks dow...

Angela Briggs-Paige, Chief People Officer at Acelero Learning, joins Rob to share why HR is not your friend—and that's a good thing. Angela breaks down how she shows up as a business leader first and a people expert always. She shares how she earned her seat at the boardroom table, what it really takes to build employee-led career paths, and why performance...

Michelle Brooks, Chief People & Culture Officer at Security Compass, joins Rob to unpack what it really means to lead with "compassionate candor." She shares how feedback norms are shifting for Gen Z, how she built a truly strategic people function without a traditional HR background, and why HR's identity crisis is holding the industry back. Plus, Michelle give...

Katya Laviolette, Chief People Officer at 1Password, joins Rob to unpack how the company scaled from a scrappy, consumer-first startup to a 1,400-person B2B security powerhouse. She shares why shifting from B2C to B2B hiring isn't just about adding new roles—it's about evolving core competencies. Katya also explains how her team uses "anti-recruiting" to scare off the wrong candidates, and how bei...

Rob reconnects with longtime friend and HubSpot's VP of Talent Acquisition & Mobility, Becky McCullough, for a conversation that spans nearly a decade of growth, both personal and organizational. Becky shares how trust, flexibility, and curiosity have kept her at HubSpot for 10+ years, and why she encourages her team to take recruiter calls (really). They also dig into HubSpot's AI-first approach to hiring, performance, and engagem...

✍️ Episode Description 

Jessica Swank didn't set out to be a Chief People Officer—but when the opportunity found her, she said yes. Now CPO at Box, Jessica joins Rob to share her unconventional career journey and how she's helping lead the company into its next era as an AI-first organization. She explains why AI is ...

Jim Conti, Talent Partner at Hyde Park Venture Partners, joins Rob to unpack what it really means to support startups from the VC side. He shares how his role has evolved from operator to advisor, why he often tells founders not to hire, and what makes a great first head of marketing hire. Jim also explains how talent leaders can earn influence without owners...

Delivery Hero's Chief People and Sustainability Officer, Ana Mitrasevic, joins Rob to challenge the status quo of performance management. Drawing on her experience in both HR and product, Ana makes the case for replacing rigid review cycles with tech-enabled, real-time performance enablement. She shares her vision of a two-sided internal talent marketplace, explains why traditional career ladders don't cut it anymore, and offers a ...

Tina Bright wasn't looking—but Inter-Con Security found her anyway. In this episode, Tina shares how a well-timed drink with the CPO turned a polite decline into a fast-tracked offer. She unpacks her playbook for entering a new org, from low-hanging fruit wins to tech stack audits, and explains why TA leaders should stay curious about the latest tools (even when they're not buying). Tina also refl...

Ken Bouchard, VP of Talent Strategy at BJ's Wholesale Club, joins Rob to break down how he led a full-scale HR transformation—without losing sight of the business. From splitting strategic and ER functions, to killing off "HR vanity projects," Ken explains how he restructured his team to be faster, sharper, and more aligned to outcomes. Plus, he shares why some projects should be shelved even if t...

Trisha Degg joins Rob to unpack her zigzagging path through sales, HR, venture capital, and back to the hiring trenches as Head of Global TA at Rush Street Interactive. She shares how "Googling her way through HR" (pre-AI!) made her a sharper TA leader, why she hired a former recruiter to wrangle ATS chaos, and how her team is using AI to reverse-engineer their best hires. From global hiring hurdl...

TTTM welcomes back Dom Farnan, who shares her journey from being the CEO of DotConnect to her current role as Head of Business Recruiting at Groq. Dom discusses the challenges and learnings from her transition, the importance of communication in leadership, and the need for a tailored recruiting process that aligns with the company's values. She emphasizes the significance of educating hiring managers about the recruitment process ...