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The CEOpeek Show

Hosted by Dave Osh · business · EN-US

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About this Podcast:

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, struggles, defining moments, and the unique “secret sauce” behind their remarkable success. Given the anonymity of Glassdoor reviews, consistently outstanding ratings from current and former employees reflect truly exceptional leadership**,** making these conversations uniquely insightful. Your host, Dave Osh, is no stranger to executive exce

Pitch Analysis

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Contact path

Public web form

Booking probability

32%

Guest openness

Selective

80/100
Required Score

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Questions about The CEOpeek Show

What is The CEOpeek Show about?

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%.

Who hosts The CEOpeek Show?

The CEOpeek Show is hosted by Dave Osh. The show has published 86 episodes to date.

What has The CEOpeek Show covered recently?

Recent episodes include "Stop Being Indispensable: The Founder’s Leadership Paradox with Evan Wong, CEO of Checkbox" (21 October 2026, 59 minutes), "First-Time CEO Learning Curve with Steven DeMaayer, CEO of Novatech" (9 September 2026, 48 minutes), and "Beyond the First Answer with James Freeman, CEO of PJ Fitzpatrick" (9 June 2026, 47 minutes).

How often does The CEOpeek Show publish?

The CEOpeek Show publishes roughly monthly, with episodes averaging 43 minutes across 86 episodes.

How hard is it to get booked on The CEOpeek Show?

Booking probability for The CEOpeek Show is 32%, and the host is rated Selective on guests. The CEOpeek Show requires a Pod Score of 80 or higher. The CEOpeek Show's contact route on record: public web form.

Who should pitch The CEOpeek Show?

The strongest fits for The CEOpeek Show are Holding Companies & Corporate HQs and Business & Management Consulting. The CEOpeek Show has a business audience.

About the host

Dave Osh hosts The CEOpeek Show, a business podcast with 86 episodes published.

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Recent episodes

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

  • Episode #25

    Stop Being Indispensable: The Founder’s Leadership Paradox with Evan Wong, CEO of Checkbox

    Oct 21, 202659 minS3

    What if being indispensable is the very thing preventing your company from growing? When Evan Wong founded Checkbox , he was the company's primary engine of execution. He worked 15–18 hours a day, built the business...

  • Episode #24

    First-Time CEO Learning Curve with Steven DeMaayer, CEO of Novatech

    Sep 9, 202648 minS3

    What happens when decades of executive experience meet the CEO chair for the first time? Steven DeMaayer stepped into his role as CEO of Novatech with more than 25 years of experience in managed IT and senior...

  • Episode #23

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

    Jun 9, 202647 minS3

    <p>What if the most important conversation is the one happening beneath the words?</p><p>James Freeman, CEO of <b>PJ Fitzpatrick</b>, believes great leadership begins by asking “the question beyond the question.”...

  • Episode #22

    Leading Through Uncertainty with Daria Leshchenko, CEO of SupportYourApp

    May 5, 202636 minS3

    <p>What does leadership look like when “normal” no longer exists?</p><p>Daria Leshchenko, CEO and Managing Partner of <b>SupportYourApp</b>, leads a global organization across rapidly changing environments while...

  • Episode #20

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

    Mar 17, 202642 minS3

    <p><b>What quietly destroys teams inside otherwise successful companies?</b><br/><br/>Not bad strategy.<br/>Not market pressure.<br/>But something much closer to home.<br/><br/>Anthony Romano has spent more than 15...

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  • Episode #21

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

    Mar 4, 202642 minS3

    <p><b>What does it really mean to lead with authenticity, especially when everything you say and do could be scrutinized?</b></p><p>Krista Snelling, CEO and Chairman of <b>West Coast Community Bank</b>, has spent nearly...

  • Episode #19

    When Being Right Holds You Back with Conor Bagnell

    Mar 3, 202641 minS3

    <p><b>What if the very thing that got you promoted is the thing that now limits your leadership?</b></p><p>When Conor Bagnell stepped into the top role at MHK, part of the Hearst Health network, he did what high...

  • Episode #18

    When Failure Becomes Your Advantage with Keith Miller

    Feb 24, 202644 minS3

    <p>What if the moments that hurt the most are the ones that quietly shape you into the leader you become?</p><p>Keith Miller doesn’t define his leadership by success. He defines it by recovery.</p><p>In this episode...

  • Episode #17

    Choosing Courage When Certainty Is Gone with Ernesto Aguilar

    Jan 20, 202641 minS3

    <p><b>What happens when playing it safe starts costing more than taking the risk?</b></p><p>Ernesto Aguilar has spent more than three decades leading through complexity—scaling firms, integrating acquisitions, and...

  • Episode #16

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

    Jan 13, 202643 minS3

    <p><b>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.</b></p><p>Travis Hess has spent more than 15 years leading global commerce...

  • Episode #15

    When Success Doesn’t Save You with Norman Radow

    Jan 6, 202648 minS3

    <p><b>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.</b></p><p>Norman Radow knows this firsthand. As the...

  • Episode #14

    When Metrics Lose Meaning with Jay Brown

    Dec 30, 202541 minS3

    <p><b>What happens when the numbers are strong—but leadership still feels off course?</b></p><p>Jay Brown, CEO of David Weekley Homes, has led at the highest levels of business, doubling the size of an S&P 500 company...

  • Episode #13

    When Leadership Follows You Home with Jordan Smith

    Dec 23, 202540 minS3

    <p><b>What if leadership didn’t end when the workday was over?</b></p><p>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...

  • Episode #12

    When Life Changes the Leader with Lance Loveday

    Dec 16, 202536 minS3

    <p><b>What happens when leadership stops being theoretical and becomes deeply personal?</b></p><p>Lance Loveday, CEO of Closed Loop, didn’t grow into a stronger leader through a new strategy or framework. His...

  • Episode #11

    Conflict Creates Alignment with Lisa Rosenthal

    Dec 9, 202543 minS3

    <p><b>What happens when a CEO builds a culture where disagreement isn’t a threat — it’s a requirement?</b><br/><br/>Lisa Rosenthal, CEO of Mayvin, leads with unapologetic transparency. She invites dissent, celebrates...

  • Episode #9

    Leading Without Looking Back with JP Hamel

    Nov 11, 202537 minS3

    <p>What happens when the very experience that built your success starts blinding you to better choices today?</p><p>JP Hamel didn’t become CEO overnight. After <b>17+ years</b> at N2—rising from franchisee to CRO...

  • Episode #10

    Leading Through the AI Shockwave with Phillip Thune

    Nov 11, 202546 minS3

    <p><b>What if the trait that once got you in trouble became your greatest leadership asset?</b></p><p>What do you do when your entire industry changes overnight?</p><p>When AI upended the search world, <b>Phillip...

  • Episode #8

    No Poker Face Leadership with Denny LeCompte

    Oct 7, 202545 minS3

    <p><b>What if the trait that once got you in trouble became your greatest leadership asset?</b></p><p>Denny LeCompte, the CEO of Portnox, has built his leadership philosophy on a foundation of unfiltered transparency...

  • The CEOpeek Show

    Good Enough Wins with Felipe Cornejo

    Sep 30, 202547 minS0

    <p>What if delivering ‘good enough’—openly and together—created better outcomes than chasing perfect in silence?<br/><br/>Felipe Cornejo, CEO and founder of Devsu, leads teams across Ecuador and the U.S., serving...

  • Episode #6

    Team-First CEO with Dylan Serota

    Sep 16, 202543 minS3

    <p><b>What if the fastest turnaround move isn’t a strategy deck—but a calendar full of one-to-ones?</b></p><p>Dylan Serota didn’t start as CEO. After co-founding Terminal inside the Atomic venture studio and serving as...

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