On the Right Stack Transistor (https://transistor.fm) https://feeds.transistor.fm/on-the-right-stack-a6e81c76-ee87-4dc4-9b37-9db88fdce1b2 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. (c) 2026 Right Stack Advisors fecd1581-ce11-5092-b25a-6aa1bbc85fc2 yes en Sun, 23 Aug 2026 21:01:09 -0700 Sun, 23 Aug 2026 21:02:21 -0700 https://rightstackadvisors.com https://img.transistorcdn.com/mHoPKksYEbKXopn-EHb2MzHoghm8x7h8hs2GjHLZP5w/rs:fill:0:0:1/w:1400/h:1400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS82Y2Yy/NTA1ODhlM2IyYjA4/MWY3NDM2MjExNWI5/ZjAyZi5wbmc.jpg On the Right Stack https://rightstackadvisors.com episodic Jason Cohen 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 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. Technology Business CEO CIO Jordan Bressler No No On the Right Stack - Episode 11 - Benjamin Bressler, Regional Airline Pilot 11 11 On the Right Stack - Episode 11 - Benjamin Bressler, Regional Airline Pilot full cdcde366-85c8-4aa6-b43e-954f00b5691b https://share.transistor.fm/s/c67098a9 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.

]]> 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.

]]> Sun, 23 Aug 2026 21:01:00 -0700 Jason Cohen Jason Cohen 1887 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.

]]> Technology Business CEO CIO No On the Right Stack - Episode 10 - Russell Kern, Founder and CEO, Kern and Partners 10 10 On the Right Stack - Episode 10 - Russell Kern, Founder and CEO, Kern and Partners full 5263eee5-2f96-4205-885f-8bfb4c39c078 https://share.transistor.fm/s/f7fa1774 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. 

]]> 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. 

]]> Sun, 16 Aug 2026 21:01:00 -0700 Jason Cohen Jason Cohen 1930 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. 

]]> Technology Business CEO CIO No On the Right Stack - Episode 9 - Carmen Baez, Founder, PRxPR 9 9 On the Right Stack - Episode 9 - Carmen Baez, Founder, PRxPR full 04401c58-e2dc-463b-a5f5-ab36096e8d9b https://share.transistor.fm/s/1477a69f 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. 

]]> 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. 

]]> Sun, 09 Aug 2026 21:00:00 -0700 Jason Cohen Jason Cohen 2382 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. 

]]> Technology Business CEO CIO No On the Right Stack - Short Stack 1 - The Human in the Loop On the Right Stack - Short Stack 1 - The Human in the Loop bonus a3fb1c47-0ca7-47d6-b206-8f8e19f1ce57 https://share.transistor.fm/s/1e803730 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. 

]]> 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. 

]]> Tue, 04 Aug 2026 08:21:57 -0700 Jason Cohen Jason Cohen 658 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. 

]]> Technology Business CEO CIO No On the Right Stack - Episode 8 - Kevin Reynolds, Founder, data4orce.ai 8 8 On the Right Stack - Episode 8 - Kevin Reynolds, Founder, data4orce.ai full 1678f8a6-3f14-49c3-9724-f47a5688a290 https://share.transistor.fm/s/94a25c9d 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. 

]]> 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. 

]]> Sun, 26 Jul 2026 21:01:00 -0700 Jason Cohen Jason Cohen 2515 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. 

]]> Technology Business CEO CIO No On the Right Stack - Episode 7 - Said Toro, CIO, Strategic Resource Technologies 7 7 On the Right Stack - Episode 7 - Said Toro, CIO, Strategic Resource Technologies full b55a8e9e-da4e-47f4-bb5d-c709847c73f4 https://share.transistor.fm/s/d0d3dd52 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. 

]]> 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. 

]]> Sun, 19 Jul 2026 21:01:00 -0700 Jason Cohen Jason Cohen 2314 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. 

]]> Technology Business CEO CIO No On the Right Stack - Episode 6 - John Chell, Former NYPD Chief of Department 6 6 On the Right Stack - Episode 6 - John Chell, Former NYPD Chief of Department full f66eb5a3-c257-46b5-953f-5df3553824af https://share.transistor.fm/s/1a98971e 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. 

]]> 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. 

]]> Sun, 12 Jul 2026 21:01:00 -0700 Jason Cohen Jason Cohen 2724 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. 

]]> Technology Business CEO CIO No On the Right Stack - Episode 5 - Anthony Viceroy, President, QH Advisors 5 5 On the Right Stack - Episode 5 - Anthony Viceroy, President, QH Advisors full d4052d43-83e9-4095-a016-2afc6a0558d3 https://share.transistor.fm/s/39e12371 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.


]]> 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.


]]> Sun, 05 Jul 2026 21:01:00 -0700 Jason Cohen Jason Cohen 3006 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.


]]> Technology Business CEO CIO No On the Right Stack - Episode 4 - Andy Roach, CEO, Triple Orbits 4 4 On the Right Stack - Episode 4 - Andy Roach, CEO, Triple Orbits full e6e42bfa-d8bd-4f3c-bcce-dc21cf49fb95 https://share.transistor.fm/s/05cf1840 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, 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. 

]]> Sun, 21 Jun 2026 21:01:00 -0700 Jason Cohen Jason Cohen 1819 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. 

]]> Technology Business CEO CIO No On the Right Stack - Episode 3 - Josh Brown, CISO, Spektrum Labs 3 3 On the Right Stack - Episode 3 - Josh Brown, CISO, Spektrum Labs full ff5097b9-8bbb-489f-8a01-2d53089e1979 https://share.transistor.fm/s/4b2aa791 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."

]]> 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."

]]> Mon, 15 Jun 2026 00:01:00 -0700 Jason Cohen Jason Cohen 2504 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."

]]> Technology Business CEO CIO No On the Right Stack - Episode 2 - Jeff Stamps, LTC Pharmacy Executive 2 2 On the Right Stack - Episode 2 - Jeff Stamps, LTC Pharmacy Executive full dd79a3f1-df3b-4786-aaec-466ce1fb533a https://share.transistor.fm/s/0e244890 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.

]]> 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.

]]> Mon, 08 Jun 2026 00:01:00 -0700 Jason Cohen Jason Cohen 2980 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.

]]> Technology Business CEO CIO No On the Right Stack - Episode 1 - Craig Walker, Founder and CEO, Dialpad 1 1 On the Right Stack - Episode 1 - Craig Walker, Founder and CEO, Dialpad full afbc5d11-0610-4ab4-ade3-194f5d0782b7 https://share.transistor.fm/s/4512cb8e 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.


]]> 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.


]]> Thu, 28 May 2026 11:56:35 -0700 Jason Cohen Jason Cohen 2596 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.


]]> Technology CEO CIO Business Leadership No