Unlearning the Old Rules of Work with CLO & Founder Monica Marquez
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Monica Marquez has held big titles at Google, EY, and Goldman Sachs, but now she’s teaching companies how to ditch their outdated playbooks and embrace a new way of working with AI. In this episode, Monica and Rob unpack why the people team, not IT, needs to lead AI transformation, how to automate without losing the human touch, and what it really means to “unlearn” your way to better work. She shares how her team at Flipwork is helping organizations build adaptive, human-centered workflows and why leaders must create safe spaces for experimentation. Also discussed: how to turn prompting...
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Candidate Screen Training Simulation with Nextdoor's Tony Castellanos
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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 alignment trumps pedigree, and how automation should empower recruiters to be more human. Also on the mic: the death of the “Apply Now” mentality, the future of AI interview agents, and...
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Wrong Fit, Right Fit: Attacking Disengagement with CLO André Martin
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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 poster, André lays out a blueprint for restoring energy, engagement, and trust inside modern organizations. Also discussed: why climbing the ladder might take you further from your craft, how companies can stop catfishing candidates, and...
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From CHRO to University of Chicago Professor with Tracy Layney
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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 down the people-side of big moves—like Levi’s exit from Russia—and shares the three-pillar framework she teaches for linking business goals to people...
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Career Passports & Manager Coaches with Acelero CPO Angela Briggs-Paige
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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 reviews need a serious glow-up. Plus: Angela’s approach to employee growth (spoiler alert: it involves passports), starting her own fractional CPO business, and never, ever being out-peopled. 📌 Key Takeaways Why HR isn’t your...
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The AI Council Opportunity with Security Compass CPO Michelle Brooks
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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 gives a front-row look at how her team is driving AI adoption across the business—from launching an internal AI council to treating AI like the biggest change management initiative of the decade. This episode is packed with...
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CPO Katya Laviolette Hires for 1Password's Hypergrowth + B2B Evolution
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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 being brutally honest during the hiring process actually leads to better retention. Plus: why every company is a train ride, and you don’t have to ride the whole way. 📌 Key Takeaways ...
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Scaling Trust & Transparency with HubSpot VPTA Becky McCullough
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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 engagement, including how they’re assessing AI fluency without bias, and why “show your prompt” might be the new “show your work.” Plus: Becky’s spicy...
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Box CPO Jessica Swank's 3-Pillar AI Framework
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✍️ 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 more about change management than tech, what it means to build cross-functional partnerships that work, and why every Boxer (even the CEO) has to pass an AI quiz. Jessica also reveals how Box rolled out an internal AI agent that writes job descriptions in seconds,...
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Bumpers in the Bowling Alley: How Talent Partners Guide Founders
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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 ownership, translate TA metrics into business outcomes, and become the first call when founders hit a crisis. Plus: the real reason boards don’t care about your hiring speed. 📌 Key Takeaways: What a talent partner actually does at an...
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Kenzie discusses her tansition from big tech to an AI startup, and how positive hiring manager relationships are more important than specific AI upskilling.
Key Points From This Episode:
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Welcoming Kenzie (Keller) Hoelscher to the show.
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Kenzie tells us about herself and how she got into recruitment.
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A little bit about Kenzie’s fascinating career.
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The importance of building relationships with your hiring managers.
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The role AI is going to play in recruiting in the future.
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How she landed up at AssemblyAI and what it’s like working there.
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The kinds of questions she asks hiring managers when sourcing.
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How Kenzie filters resumes to narrow down her search.
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Kenzie shares some advice for anyone who wants to get into AI.
Quotes:
“With any role while you’re recruiting, as long as you’re having those conversations with your hiring manager and understanding what those main skillsets are, I do think it’s easy to go out there and source for them.” — Kenzie (Keller) Hoelscher [22:48]
“There’s definitely risks to being in a startup but I think now we’re seeing that there’s risks at being at bigger companies as well so why not take the risk?” — Kenzie (Keller) Hoelscher [30:40]
“AI is a booming industry [and] there’s a lot of energy around it right now.” — Kenzie (Keller) Hoelscher [31:24]
Links Mentioned in Today’s Episode:
Kenzie (Keller) Hoelscher on LinkedIn