Lead the Team (Top 2% of Podcasts)

The bigger your company gets, the more polished reports can distort vital truth. In this episode of Lead the Team, Ben Fanning sits down with John Case, CEO of Acumatica and former Microsoft executive who helped scale Office 365 into one of the most successful cloud businesses in the world. John shares why one of the most important responsibilities of leadership is creating direct access to truth...

AI is changing leadership faster than most executives realize, pushing teams to move at a speed that introduces multi-million dollar operational blindspots. In this episode of Lead The Team, Ben Fanning sits down with Radha Basu, Founder & CEO of iMerit, to break down why "right beats fast" when scaling technology. Discover how to navigate high-stakes AI disruption, structure true organization...

AI IS REBUILDING LEADERS KK, CEO of Ascendion, believes most companies are still thinking about AI too small-scale. The leaders pulling ahead are rebuilding how they operate. And that’s a very different conversation! KK walked away from one of the world’s largest IT services companies because he could already see the old model starting to crack: More headcount. More layers. More complexity. Meanwh...

Comfort Stops Growth. Magen Buterbaugh, President & CEO of Greene Tweed, walked away from leading a billion-dollar business at DuPont because she realized something… Success can become a trap. Her role was secure. The path was clear. The reputation opened doors. But she knew she had stopped growing. So she left the corporate safety net to help build a startup with one employee, real payroll pr...

Most leaders are preparing for the wrong enemy. Matt Thompson, President and Chief Commercial Officer at Socure, is helping lead the fight—where machine identities already outnumber humans 80 to 1. And fraud isn’t just growing… it’s evolving faster than most businesses can keep up. Most leaders are still treating this like a tech problem. It’s not. It’s truly a strategy problem. The adversary is d...

Pressure reveals leaders. Keval Hutheesing, CEO of Cygnet. One, was 25 when he suddenly became responsible for 900 people—in the middle of a crisis. No playbook. No certainty. And hundreds of people counting on his decisions. Most people think leadership in moments like that is about having the "right" answers. That’s the mistake. As Keval told me: “I didn’t have all the information… but I had our...

Getting AI Wrong Arun Varadarajan, Chief Commercial Officer at Ascendion, reframed how I think about why so many AI initiatives are failing. “90% of projects fail because people don’t spend enough time defining the problem.” Not because the technology failed or the team wasn’t smart enough. It's because leaders started building BEFORE they got clear on what actually needed to change. So what looke...

The Scaling Mistake Hightouch CRO, Josh Kanagy, showed me how companies scaling fastest right now are creating their biggest future leadership problem. Companies are obsessed with scaling: • systems • process • AI • automation Yes, those things matter. BUT there’s a real danger when leaders start believing scaling the system automatically scales the company. Josh learned that the hard way in a hum...

Do you know BRUCE? Andy Freed, Chairman of Virtual, Inc. has seen Bruce Springsteen nearly 100 times, and was so inspired by what he saw that he wrote a book about it.... ...Lead Like The Boss: The Bruce Springsteen Framework to Elevating Your Leadership What Andy took from those shows completely changed how he leads. For instance at the end of every show, Bruce walks to the back of the stage… …an...

Why Leave Success? monday.com CRO Case George once got career advice he never expected. After decades at IBM a close mentor looked at him and said: “I’ll deny it if you tell anybody… but I think you should leave.” It was unexpected but that advice changed everything for Case. He went on to help scale billion-dollar revenue organizations and now leads global revenue at monday.com, a platform used b...

They Said Don’t. Andrew Brandman, COO of DailyPay and a former leader at the New York Stock Exchange, knows risk taking When he decided to join the NYSE back in the day, everyone told him he was making a mistake. “Everyone was saying to me, don’t do it!.” He did it anyway. That decision didn’t just work out — it actually put him at the center of transforming a 200+ year old institution and reshape...

Fastest Tech Adoption in History. Zoom COO Aparna Bawa was right in the middle of it... helping lead the company as the entire world moved onto one platform in a matter of weeks. For work. For school. Even for final goodbyes. I sat down with Aparna to understand what leadership actually looked like in that moment. One decision changed it all... They turned Zoom on for K–12 schools across the U.S.—...

Inside the Room. Hayden E. Stafford, President & CRO at Seismic, had a front-row seat to Satya Nadella rebuilding Microsoft from the inside out. The world saw the outcome. Hayden saw the decisions. The ones that got challenged. The ones that got changed. And the ones leaders refused to change. He saw that alignment didn’t break all at once. It broke when signals said something isn’t working… a...

AI isn’t accountable. Leaders are. Eileen Sweeney, PROS CRO, operates in a world where algorithms influence billions in airline revenue. The scale and speed are staggering. What a conversation on a big idea that leaders and teams are challenged by right now... When algorithms shape decisions… who owns the outcome when it goes wrong? Not the system. The leader. You see it in high-stakes deals—every...

Looks Like Progress. It’s Not. So I asked Adrian Stoch, CEO Americas at Hai Robotics: What’s the mistake that looks right… but costs millions? Why do “working” systems still fail? What breaks first when you scale? He’s led automation at massive scale. Inside Target. Inside GXO. Now leading robotics. He told me about one warehouse…Robots installed. Systems live. Dashboards green. It looked like pro...

After 10,000 Interviews... Rod McDermott, CEO of McDermott + Bull and founder of Activate 180, has noticed that the executives who win interviews… ...aren’t always the ones who build results. And that’s the trap. It's so easy to fall for the wrong signals. The leader who owns the room. The polished answers. The one who leaves everyone thinking, “That was impressive.” But impressive DOESN'T SCALE....

Noise vs Focus. Bob McCuin, Chief Revenue Officer and EVP at Clear Channel Outdoor, has spent decades inside the attention economy...radio, sports media, and literally the most valuable billboards on the planet. When you live in that world long enough, you start to notice something about leadership. What's shaping how organizations behave. Bob told me that attention determines priority. Most leade...

Leadership Blindspot Adam Block, Chief Revenue Officer at Motive, who helped scale the company to serve 100,000+ customers and more than a million drivers, shared a real wake up call with me. Early in his career, he spent a lot of energy trying to help struggling employees succeed. Then he realized something uncomfortable. “The people that suffer the most in that situation are actually the best pl...

My AI just joined the meeting... I expected Abhijit Mitra, CEO of Outreach, a multi billion-dollar AI company, to tell me about their legendary tools and automation. Instead, he it took a different direction. When he’s in a meeting… his AI agents actually join the meeting and coach him in real time. Not summarize it later. Not send notes afterward. They’re in the meeting, helping him think, respon...

Lives Depend. Parker Burke, Group President at Fluke Corporation, leads an organization whose tools help technicians safely test electrical systems in power grids, hospitals, factories, data centers, and mines around the world. So when a technician trusts the reading on a device…they’re trusting it with their life. A 99% success rate isn’t success. Because the remaining 1% can mean catastrophe. Th...

Details Define You. Bob Hughes, President & CEO of Deltek, learned that in moments when the stakes were highest.. on a nuclear submarine… in the middle of a $22B merger… and during a ransomware attack. He was inspired early in his career when a leader told him: “The devil’s in the details… but so is salvation.” I particularly appreciated his insight: “Operational discipline scales trust.” We’v...

Elite CEOs and athletes share a belief. Usman Shuja, CEO of Bluebeam, learned it long before the boardroom, representing the USA national cricket team and becoming one of the top wicket-takers in U.S. history. Talking with him made me think about how differently pressure shows up across seasons of life. In sports, the pressure is loud and public. In leadership, it even heavier....Board expectation...

Google’s “Wolverine” is now a $100M+ CEO Keith Rabkin, CEO of PandaDoc, is one of the few leaders I’ve met who can bridge the gap between "big-tech discipline and scrappy underdog grit". At Google, Keith was one of only 25 people (out of thousands of geniuses) to win the "Great Manager Award." His secret isn't just a high IQ; it's what he calls the "Wolverine Mindset" . It’s a relentless, "never-g...

THE TRANSFORMATION WALL Randall Troutman, Winpak's, Chief Operational Excellence Officer leads a massive $1.1 billion transformation, tasked with turning 13 independent "kingdoms" into one efficient operating system. But there’s a moment in every change effort where leaders mistake resistance for failure, and that’s when teams stop following. Randall discovered that project success is never about...

Leaders Are Built in the Blur. Jed Ayres, CEO of ControlUp, told me something most leaders won’t say out loud: Clarity usually comes after you move, not before. If you’re waiting for the perfect signal…You’re already late. That “responsible” decision you’re about to make? It might be the very thing slowing your flywheel before it ever turns. We talked about what it really takes to move when things...