Fit Happens: The Executive Search Podcast

Your best salesperson just got promoted to manager. Here's why that's often a mistake. In this solo episode, Jason Baumgarten unpacks the Peter Principle, the half-century-old idea that people in a hierarchy rise to their level of incompetence, and the 2019 study that proved it's not just a joke. Drawing on research covering tens of thousands of salespeople across more than 130 companies, Jason br...

If time is your most valuable asset, who's actually deciding how yours gets spent? In this solo episode, I unpack a paradox I see constantly in the leaders I work with: real authority over strategy and budget, almost none over their own calendar. I introduce the idea of designed time versus default time, walk through the three traps that quietly steal a leader's week, and give you a simple three-q...

What if the same leader, running the same playbook, could fail in one place and win big in another? That's the question at the heart of my conversation with Jim Citrin, who has spent three decades at the top of the executive search world placing and advising CEOs. Jim is also one of my mentors, so we go past the usual hiring talk into what actually decides whether a leader succeeds: fit. We trace...

What if the thing quietly undermining your team's performance isn't strategy, compensation, or culture decks, but whether people feel like they matter? Jennifer Wallace is a journalist and award-winning author of Never Enough and her newest book, Mattering . She spent years studying what allows people — children, employees, leaders — to thrive under pressure, and her answer centers on a deceptivel...

The boardroom is the last line of defense for AI governance — and most directors aren't ready. Steven Wolfe Pereira has spent 30 years at the intersection of technology, data, and leadership — from building the early internet at Akamai to now running Alpha, the AI governance intelligence firm reshaping how boards and C-suite executives prepare for the agentic era. In this conversation, Jason and S...

What if the job you have today quietly becomes the job you never agreed to take? In this solo episode, Jason Baumgarten breaks down one of the most underestimated risks facing leaders right now: not job replacement, but job transformation. Drawing on history, academic research, and real examples from his work in executive search, Jason explains how AI and automation are quietly unbundling roles fr...

The investors closest to the best founders have a front-row seat to what great fit really looks like. In this episode of Fit Happens, I sit down with Laela Sturdy, Managing Partner at CapitalG — Alphabet's growth investment fund — and one of the most thoughtful voices on leadership fit I've encountered. Laela has spent 20 years inside Google and Alphabet and 13 years partnering with hyper-growth c...

You have roughly 4,000 weeks. Are you spending them on work that actually deserves them? In this solo episode, Jason Baumgarten — senior partner and executive search specialist — explores one of the most under-examined questions in leadership: the relationship between fit and time. Drawing on Oliver Burkeman's 4,000 Weeks , decades of executive search experience, and insights from organizational p...

Dan Gertsacov, CEO of Big Green Egg, has built a career by saying no to money and yes to fit — four times over. In this episode, we dig into his non-linear path from social entrepreneur to Google exec to restaurant industry leader, and how each chapter prepared him for the challenge of revitalizing one of America's most iconic brands. Dan shares the ikigai framework he has used to navigate every m...

Most executives aren't failing loudly — they're quietly eroding from the inside out. Nearly a quarter of CEOs report feeling burned out daily. But burnout isn't just a personal problem — it's an organizational risk that degrades judgment, shortens vision, and quietly erodes the very leadership capacity your organization depends on. In this episode, I break down a simple, actionable model for susta...

What does it really take to find the role you were built for — and lead it at scale? In this episode of Fit Happens, I sit down with Scott Pulsipher, CEO of Western Governors University, to explore how a former Amazon leader found the most meaningful fit of his career — and what it cost him to get there. Scott opens up about a brutal leadership feedback experience at Amazon that nearly broke his c...

Most executives fail not because they lack talent — but because they're solving the wrong problem. In this solo episode of Fit Happens, I'm breaking down the single most important sentence any executive can write: "I was hired to do X, as measured by Y, while avoiding Z, and by building systems and teams that make it repeatable." Whether you're stepping into a new C-suite role or six months into o...

She left a dream job at peak success — because she finally discovered what true alignment feels like. In this episode of Fit Happens, Jason Baumgarten sits down with Kara Nortman, managing partner of Monarch Collective — the only investment platform exclusively focused on women's sports. Kara's career spans Morgan Stanley, IAC, Battery Ventures, Upfront Ventures, and co-founding Angel City Footbal...

Most people are winging one of the most important decisions of their lives. What's the difference between someone who springs out of bed Monday morning and someone who drags themselves there? It's not salary. It's not title. It's fit — and it's backed by over a century of science that most of us are ignoring. In this premiere episode of Fit Happens, Jason Baumgarten breaks down the five levels of...