On the Right Stack is a podcast for business leaders, executives, and technology decision-makers who want to cut through the noise and build technology strategies that actually work. Each episode features candid conversations with seasoned operators, CTOs, CISOs, and CEOs sharing hard-won insights on tech strategy, transformation, and leadership. We don’t talk about technology for technology’s sake — we talk about the decisions that move businesses forward. Hosted by Right Stack Advisors, where smarter technology decisions start.
On the Right Stack - Episode 11 - Benjamin Bressler, Regional Airline Pilot
In this episode of On the Right Stack, Jason steps away from technology to tell a story about dreams. His guest, Benjamin Bressler, recently became a pilot for a regional airline, capping a goal he first set at age ten. Benjamin walks through the training hurdles, a failed first check ride, and the financial and personal sacrifices that came with chasing an expensive dream. He describes the shock of the job offer, his first takeoff, and the imposter syndrome of walking through the terminal in uniform. A grounded reminder that persistence pays off.
17 Aug 2026
On the Right Stack - Episode 10 - Russell Kern, Founder and CEO, Kern and Partners
On this episode of On the Right Stack, host Jason Cohen sits down with Russell Kern, the serial entrepreneur who built one of Omnicom's first true data-driven precision marketing agencies. Russell grew Kern from a startup into the firm that helped scale DirecTV, T-Mobile, and Sprint before Omnicom acquired it. The conversation moves from precision marketing to leadership, covering why customer understanding is an organizational problem and not a data problem, how to treat AI as a power tool without surrendering human judgment, and why humility and vulnerability are lasting leadership strengths.
10 Aug 2026
On the Right Stack - Episode 9 - Carmen Baez, Founder, PRxPR
Carmen Baez spent decades helping Omnicom expand across Latin America, then built something entirely different. In this episode of On the Right Stack, the former president of DAS Latin America and founder of PRxPR joins Jason Cohen to talk leadership, adaptability, and purpose. She shares why people are the whole game, how she navigated 20 distinct markets rather than one monolithic region, and what Hurricane Maria taught her about urgency. Her nonprofit sends every donated dollar straight to communities. This is a conversation about business, philanthropy, and the leadership fundamentals that never change.
4 Aug 2026
On the Right Stack - Short Stack 1 - The Human in the Loop
Most organizations assume newer technology means better service. Three guests from three different worlds arrived at the opposite conclusion. In the debut of Short Stack, a pharmacy technology executive, a career sales leader, and the CEO of a community center each found that the technology was rarely the thing that broke. We keep pointing it at the wrong thing. From frustrating phone trees to seniors asking not to use an app, this episode makes a simple case. The work is not to replace people. It is to clear the things people should not have to do.
27 Jul 2026
On the Right Stack - Episode 8 - Kevin Reynolds, Founder, data4orce.ai
On this week’s episode, host Jason Cohen reconnects with Kevin Reynolds, a MarTech and data veteran whose 25-year career spans Omnicom, NBCUniversal, and Publicis, and who recently founded data4orce.ai, a startup helping CPG brands, retail media networks, and publishers monetize first-party data. Kevin explains why platform selection should start with business goals and KPIs rather than shiny objects, why change management belongs at the very beginning of every implementation, and how AI is transforming customer data. He also breaks down the shift from per-seat to outcome-based pricing, and why legacy systems still deserve respect.
20 Jul 2026
On the Right Stack - Episode 7 - Said Toro, CIO, Strategic Resource Technologies
Said Toro has spent 26 years leading enterprise strategy and digital transformation across manufacturing, healthcare, financial services, and private equity. In this episode of On the Right Stack, he and host Jason Cohen examine how the CIO role has moved from the back office to the boardroom, and why business fluency now matters more than technical depth. The conversation covers speaking the language of EBITDA and exit readiness, why cybersecurity is a business problem rather than an IT one, cutting through the noise around AI, and a practical framework for a CIO's first 100 days.
13 Jul 2026
On the Right Stack - Episode 6 - John Chell, Former NYPD Chief of Department
Leadership is easy when everything is going right. The real test comes under pressure, when information is incomplete and every decision carries weight. In this episode, Jason Cohen sits down with John Chell, former NYPD Chief of Department, for a conversation about leading people through uncertainty. Drawing on a 32-year career, Chell shares what holds a team together in a crisis, why communication fails first, and where AI genuinely helps. The lessons apply to any leader in any field.
6 Jul 2026
On the Right Stack - Episode 5 - Anthony Viceroy, President, QH Advisors
What does it actually take to build an organization worth leading? Anthony Viceroy spent decades answering that question. As the former CEO of WestMed Medical Group, he grew a beloved regional healthcare brand through intentional culture-building, disciplined growth, and a leadership philosophy centered on people. He went on to serve as President and COO of Summit Health and COO of VillageMD. In this conversation with host Jason Cohen, Anthony reflects on what separates good leaders from great ones, how culture drives technology adoption, and why the people side of transformation is the most rewarding part to get right.
22 Jun 2026
On the Right Stack - Episode 4 - Andy Roach, CEO, Triple Orbits
In this episode, host Jason Cohen reconnects with longtime colleague Andy Roach, Founder and CEO of Triple Orbits Technology. Andy brings nearly three decades of experience building technology for knowledge workers across professional services and the automotive industry.
The conversation covers what responsible AI adoption actually looks like inside an organization: governance, data protection, and why people and process have to come before any technology decision. Andy also shares his take on the AI hype worth ignoring, why creativity can never truly be replaced, and what the next decade might hold for the generation growing up as AI natives.
15 Jun 2026
On the Right Stack - Episode 3 - Josh Brown, CISO, Spektrum Labs
In this episode of On the Right Stack, host Jason Cohen sits down with Joshua Brown, a seasoned CISO and cybersecurity leader with more than 25 years of technology experience.
The conversation debunks the "dark art" of technical security, reframing cyber risk as a critical business problem rather than just an IT issue. Joshua cuts through the current AI hype, breaks down why compliance programs are failing to produce better security outcomes, and highlights why the best defense is mastering unsexy basics like patch management. He also shares firsthand leadership lessons on managing a crisis, earning credibility at the board table, and avoiding the trap of becoming the "department of no."
8 Jun 2026
On the Right Stack - Episode 2 - Jeff Stamps, LTC Pharmacy Executive
Host Jason Cohen sits down with Jeff Stamps, a pharmacist and healthcare leader with decades of experience in long-term care pharmacy, who guided a company through rapid growth, a global pandemic, and a successful acquisition.
They get candid about what makes technology leadership actually work: the four traits of a great CIO, why cybersecurity has to be a top priority before disaster strikes, where AI is genuinely useful in healthcare, and how to earn a real seat at the executive table. A practical, jargon-free look at how leadership and technology come together to drive results.
28 May 2026
On the Right Stack - Episode 1 - Craig Walker, Founder and CEO, Dialpad
Not every technology decision gets made in Silicon Valley, and that is exactly the gap this podcast was built to close. Host Jason Cohen sits down with Craig Walker, founder and CEO of Dialpad, bringing a veteran operator’s perspective to a conversation about unified communications, early AI adoption, and what it takes to lead technology transformation at any scale. Real experience. Real insight. No hype.
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Apple Podcasts (US)
5.0 / 5
4 ratings
Spotify
5.0 / 5
2 ratings
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