Dave Osh

The CEOpeek Show

Business EN ↓ 84 episodes

The CEOpeek Show is a podcast where exceptional leadership stories unfold. Hosted by Dave Osh, this podcast brings you intimate, deep-dive conversations with some of the most admired CEOs in the corporate world—leaders whose companies consistently earn stellar Glassdoor ratings (typically around 4.5 stars) and impressive Glassdoor CEO approval rates higher than 90%. Now in its third season with over 60 episodes published, The CEOpeek Show has evolved into long-form, authentic discussions, uncovering the raw, honest realities of leadership. Our guests courageously share their personal journeys,...

Author

Dave Osh

Category

Business

Podcast website

www.ceopeek.com

Latest episode

Jun 9, 2026

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Episodes

Beyond the First Answer with James Freeman, CEO of PJ Fitzpatrick 09.06.2026

What if the most important conversation is the one happening beneath the words? James Freeman , CEO of PJ Fitzpatrick , believes great leadership begins by asking “the question beyond the question.” Instead of accepting the first answer, he teaches leaders to look deeper—to uncover potential, understand what truly matters to people, and help them become more than they thought possible. Since becom...

Leading Through Uncertainty with Daria Leshchenko, CEO of SupportYourApp 05.05.2026

What does leadership look like when “normal” no longer exists? Daria Leshchenko , CEO and Managing Partner of SupportYourApp , leads a global organization across rapidly changing environments while continuing to scale an international business and distributed teams around the world. Taking over the company at just 21, Daria scaled it into a multinational operation with over 1,200 people across 8 g...

The Leadership Mistake That Breaks Teams with Anthony Romano, CREtelligent CEO 17.03.2026

What quietly destroys teams inside otherwise successful companies? Not bad strategy. Not market pressure. But something much closer to home. Anthony Romano has spent more than 15 years leading growth and transformation across the real estate finance and mortgage technology industries. Today, he serves as CEO of CREtelligent , a commercial real estate due diligence and risk management firm he joine...

The Power of Authentic Leadership with Krista Snelling, CEO of West Coast Community Bank 04.03.2026

What does it really mean to lead with authenticity, especially when everything you say and do could be scrutinized? Krista Snelling, CEO and Chairman of West Coast Community Bank , has spent nearly three decades in banking and leadership. In an industry built on trust, regulation, and reputation, she has learned that leadership isn’t about managing perception—it’s about consistency of character. I...

When Being Right Holds You Back with Conor Bagnell 03.03.2026

What if the very thing that got you promoted is the thing that now limits your leadership? When Conor Bagnell stepped into the top role at MHK , part of the Hearst Health network, he did what high performers do — he provided answers. When his team asked for alignment, he went away, built the strategy himself, and brought it back. What he got in return wasn’t momentum. It was silence. That moment f...

When Failure Becomes Your Advantage with Keith Miller 24.02.2026

What if the moments that hurt the most are the ones that quietly shape you into the leader you become? Keith Miller doesn’t define his leadership by success. He defines it by recovery. In this episode, Keith reflects on the setbacks that tested him — the operational missteps, the financial pressures, and the hard lessons that forced him to grow faster than he wanted to. Instead of hiding those mom...

Choosing Courage When Certainty Is Gone with Ernesto Aguilar 20.01.2026

What happens when playing it safe starts costing more than taking the risk? Ernesto Aguilar has spent more than three decades leading through complexity—scaling firms, integrating acquisitions, and making decisions where certainty was never guaranteed. In this conversation, Ernesto reflects on the moments when caution felt responsible—but courage turned out to be essential. We talk about fear not...

Built in the Hard Moments with Travis Hess, CEO of BigCommerce 13.01.2026

Some leadership lessons don’t come from wins—they come from the moments that test who you are when things don’t go as planned. Travis Hess has spent more than 15 years leading global commerce organizations, advising boards, scaling businesses, and navigating high-stakes transitions. Today, as CEO of Commerce, he carries responsibility for a global platform and thousands of customers. But in this c...

When Success Doesn’t Save You with Norman Radow 06.01.2026

You can survive a bad deal. You can even recover from a failed strategy. But some leadership mistakes don’t announce themselves—and they don’t fade quietly. Norman Radow knows this firsthand. As the Founder and CEO of The RADCO Companies , Norman has led more than 150 real estate turnarounds, transforming distressed assets into thriving communities and building one of the most respected multifamil...

When Metrics Lose Meaning with Jay Brown 30.12.2025

What happens when the numbers are strong—but leadership still feels off course? Jay Brown , CEO of David Weekley Homes , has led at the highest levels of business, doubling the size of an S&P 500 company while building a culture rooted in trust, transparency, and people-first performance. In this conversation, Jay challenges a quiet leadership trap: when metrics pull our attention downward, le...

When Leadership Follows You Home with Jordan Smith 23.12.2025

What if leadership didn’t end when the workday was over? In this episode, Jordan Smith , the CEO of Jet Dental , challenges one of the most comfortable myths in leadership: that work and life can be cleanly separated. Drawing on lived experience and deep reflection, Jordan explores how the quality of a leader’s day at work doesn’t stay at work—it ripples into families, relationships, and the lives...

When Life Changes the Leader with Lance Loveday 16.12.2025

What happens when leadership stops being theoretical and becomes deeply personal? Lance Loveday , CEO of Closed Loop , didn’t grow into a stronger leader through a new strategy or framework. His transformation came through life itself. After losing his father, Lance found that grief reshaped how he showed up—not just as a person, but as a CEO. What emerged was a deeper commitment to his values, gr...

Conflict Creates Alignment with Lisa Rosenthal 09.12.2025

What happens when a CEO builds a culture where disagreement isn’t a threat — it’s a requirement? Lisa Rosenthal , CEO of Mayvin , leads with unapologetic transparency. She invites dissent, celebrates challenge, and believes alignment is only possible when people are willing to say the uncomfortable things out loud. In her world, “conflict” isn’t chaos — it’s clarity. And she pushes her teams to em...

Leading Without Looking Back with JP Hamel 11.11.2025

What happens when the very experience that built your success starts blinding you to better choices today? JP Hamel didn’t become CEO overnight. After 17+ years at N2—rising from franchisee to CRO, President, and now CEO—he’s seen the full loop: trying, failing, trying again, and learning when to let go of what used to work. In this candid conversation, JP shares how long-tenured leaders can use h...

Leading Through the AI Shockwave with Phillip Thune 11.11.2025

What if the trait that once got you in trouble became your greatest leadership asset? What do you do when your entire industry changes overnight? When AI upended the search world, Phillip Thune , CEO of Adthena , faced a leadership crucible few CEOs ever encounter: transform the company’s core business or risk being left behind. In this gripping conversation, Philip shares how he and his team spen...

No Poker Face Leadership with Denny LeCompte 07.10.2025

What if the trait that once got you in trouble became your greatest leadership asset? Denny LeCompte, the CEO of Portnox, has built his leadership philosophy on a foundation of unfiltered transparency. He owns his mistakes in company-wide emails, actively invites dissent, and aligns his teams by always sharing the complete picture. A former cognitive psychology PhD turned tech leader, Denny reveal...

Good Enough Wins with Felipe Cornejo 30.09.2025

What if delivering ‘good enough’—openly and together—created better outcomes than chasing perfect in silence? Felipe Cornejo, CEO and founder of Devsu, leads teams across Ecuador and the U.S., serving clients throughout the Americas. Early on, a live ESPN launch nearly went sideways when performance tests were missed—and the team hesitated to surface the risk. That moment catalyzed a leadership st...

Team-First CEO with Dylan Serota 16.09.2025

What if the fastest turnaround move isn’t a strategy deck—but a calendar full of one-to-ones? Dylan Serota didn’t start as CEO. After co-founding Terminal inside the Atomic venture studio and serving as Chief Strategy Officer, he stepped into the top job during a brutal reset—RIFs, salary cuts, and a near refounding. His first act: meet every single employee one-on-one to rebuild trust, alignment,...

The Leader Who Rejects Autocracy with Chad Hesters 02.09.2025

Do CEOs really need to control everything—or is that the fastest way to kill innovation? Chad Hesters, President & CEO of Boyden, learned early in his career—first as a U.S. Naval Intelligence officer and later in the corporate world—that the most effective leaders are not autocrats at the top of the pyramid. Instead, the best leaders empower others, build trust, and create organizations where...

Lead Without Fear with Marc Zionts 12.08.2025

The most trusted leaders aren’t the ones who avoid conflict—they’re the ones who step into it with courage and clarity. Marc Zionts has built an extraordinary international career, leading companies across Israel, India, Japan, China, and beyond. As the CEO of SundaySky, he believes that leadership means making the hard calls, being radically transparent, and fostering trust through direct, honest...

The Leader Who Finds Joy in Service with Ben Kessler 04.08.2025

What if the secret to true leadership isn't chasing outcomes but embracing genuine service? Ben Kessler discovered the core of his leadership philosophy at a surprisingly young age when his father taught him that true joy emerges from serving others. From nearly becoming a Catholic priest to navigating the challenging world of McKinsey consulting and eventually becoming CEO of 66degrees, Ben’...

When Tragedy Shapes Purpose with Harry Bruell 15.07.2025

What happens when your deepest personal tragedy reshapes your purpose and transforms your approach to leadership? Harry Bruell spent 25 years passionately leading conservation efforts, growing small regional programs into a nationwide movement. But in 2016, the unimaginable happened—Harry lost his 14-year-old daughter to suicide. This profound loss became a pivotal turning point, compelling Harry...

The Leader Who Survived a Nightmare Boss with Brian Underhill 07.07.2025

We've all had difficult bosses, but what happens when your first boss is straight out of Hollywood’s worst nightmares? Brian Underhill started his career under a toxic boss who screamed, cursed, and threw objects at him, leading Brian to question everything about work and leadership. Instead of breaking him, this experience inspired Brian to become obsessed with transforming the way leaders l...

Creating a Diverse and Inclusive Workplace - Wynne Nowland, CEO, Bradley & Parker 19.05.2022

In this revealing interview, Wynne Nowland, Bradley & Parker CEO, shares her simple, yet powerful worldview of expansive and united leadership. Bradley & Parker is a premier insurance, risk management, and financial services firm founded in 1939 in Long Island, New York.  With more than 15,000 clients, including publicly traded companies with complex global insurance programs and the large...

Leading Globally in High Complexity - Paula Schneider, CEO, Susan G. Komen 12.05.2021

In this insightful interview, Paula Schneider, Susan G. Komen CEO, reveals the leadership lessons she learned from leading global organizations. Susan G. Komen is a global movement that, over 30 years, has led the way in funding $3 billion in groundbreaking research, community health initiatives, and advocacy programs in local communities across the U.S. and in more than 30 countries, serving mill...

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