Unlearning the Old Rules of Work with CLO & Founder Monica Marquez
Talk Talent To Me
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Marquez has held big titles at Google, EY, and Goldman Sachs, but now she’s teaching companies how to ditch their outdated playbooks and embrace a new way of working with AI.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...
info_outlineWhat does it take to build a people-first hiring culture from the ground up, without sacrificing speed or scale? In this episode of Talk Talent to Me, returning guest Anna Chalon, Head of People at Runway, shares how she intentionally navigated her career from startup to acquisition and back again, fueled by a love for building and a clear sense of purpose. She unpacks her criteria for choosing the right company, the power of gut instinct balanced with measurable data, and how candidate experience can be both human and scalable. Anna also offers insights into how she assesses founders during interviews and why speed and thoughtfulness in hiring are good indicators of long-term cultural alignment. Tune in to learn how to build resilient, high-trust recruiting processes and make smarter career decisions rooted in self-awareness and intention!
Key Points From This Episode:
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An overview of Anna’s journey from Frame.io to Adobe to Runway.
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How she used Adobe’s acquisition of Frame.io as a career checkpoint.
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The importance of being clear about the size and pace of the company you want.
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Values over industry: the creative culture and visionary founders that drew Anna to Runway.
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Founder responsiveness as a hiring signal (and what to look for in the first interview).
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Reflecting on hiring wins and misses as opportunities to learn and improve.
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Blending data and intuition to ensure that a role truly excites you.
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Building scalable, human-centered hiring from scratch with speed, structure, and soul.
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The impact of timely check-ins, personal touches, and radical hiring transparency.
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Starting lean but thinking long-term: balancing agility with a premium candidate experience.
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The power of seeking out quick wins to add value in the short term.
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A simple strengths-enjoyment framework for informed career decisions.
Quotes:
“Even though I'm not going to be using the product every day, the company culture is still shaped by the type of tool you create.” — Anna Chalon [08:15]
“[Hiring] is not a perfect science. All these things are still human-based decisions at the end of the day. You do the best with the information you have.” — Anna Chalon [14:44]
“My goal when I'm building these foundations is: how do we have enough structure and repeatability that we could hire 100 people – if we need to but every single candidate [also feels] like they're alone in the process?” — Anna Chalon [19:14]
“Any kind of communication is better than ghosting. – When people are looking for a job, anxiously waiting to get a response, it's just not the right thing to do.” — Anna Chalon [26:24]
“What am I good at? What do I like? What is the overlap? And how does that apply to work?” — Anna Chalon [37:52]
Links Mentioned in Today’s Episode: