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. 

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. 

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 thirty-two 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. 

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.

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. 

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.”

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.

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.