Tech Whisperers: Inside the Playbooks of the Best Digital Leaders

Phillip Dundas, Chief Technology Officer at AlTi Global, is the kind of leader who injects optimism, conviction, and a deep commitment to trust into everything he does. Over the course of his career leading technology at complex financial institutions, Phil has learned that sustainable transformation starts with strong foundations, trusted data, genuine relationships, and people who understand how their work connects to the bigger picture. Whether he’s leading a technology organization or pedaling 3,500 miles across the country with his family, his approach is grounded in staying focused on the destination while remaining willing to change the route along th...

With AI turning the traditional leadership playbook on its head, many leaders are finding themselves stuck in cycles of pilots, experimentation, and uncertainty. Marianne Johnson, EVP & Chief Product Officer at Cox Automotive, is one of the select few who are already creating real business impact, rewriting the playbook and redefining what’s possible in the process. In this episode of Tech Whisperers, we’re shining a light on Marianne’s enterprise leadership story, which involves orchestrating one of the largest business transformations in the industry, grounded in the conviction that AI starts and ends with people.Marianne shares...

While many leaders spend their careers trying to avoid uncertainty, GE Aerospace CIO David Burns has built his by embracing it. After more than 25 years leading through transformation, disruption, and some of the biggest moments in modern business and technology, David has developed a leadership philosophy rooted in continuous learning, developing people, and helping teams thrive when the path ahead is anything but clear.In this episode of Tech Whisperers, we are shining the light on David’s journey and exploring what it takes to lead through turbulence, build high-performing teams, create a culture of continuous improvement, an...

Jane Connell began her career without a college degree and no pre-determined path to executive leadership. Yet through grit, curiosity, authenticity, and an unwavering belief that leadership is ultimately about people, she has built one of the most respected careers in technology. In this episode, we are shining the light on Jane’s remarkable journey ahead of her induction into the CIO Hall of Fame.Through a diverse group of Mystery Questioners who help us answer the question “What Would Jane Do?” Jane is sharing the leadership philosophies, career-defining moments, and deeply personal lessons that shaped her four-d...

While many leaders will put technology and innovation at the center of the story, Sal Companieh, Chief Digital & Information Officer at Cushman & Wakefield, keeps people, trust, and authentic relationships at the center instead. In this episode of Tech Whisperers, Sal sits down with host Dan Roberts for one of the most thoughtful leadership conversations we’ve ever featured.We’re unpacking Sal’s leadership playbook to learn how empathy, curiosity, trust, and human connection have become the foundation of innovation at scale inside a 53,000-person global organization.Connect with Sal: https://www.linkedin.com/in/salume...

What does successful leadership look like in the age of AI, constant disruption, and accelerating change? In this episode, Dan Roberts sits down with Sears Merritt, CIO at MassMutual. Rather than chasing headlines, Sears has spent more than a decade building systems, teams, and cultures that consistently deliver impact, all while staying deeply grounded in purpose, accountability, and policyholder-first service.We are unpacking Sears’ leadership playbook to learn how MassMutual approaches innovation inside a 175-year-old institution, why adaptability is becoming a timeless leadership skill, and how organizations can create environments where breakthrough thinking naturally emerges.Co...

Today’s guest is a technology executive who has mastered the art of honoring a strong legacy while reinventing it in an era of massive disruption. Leigh-Ann Russell is the CIO and Global Head of Engineering at BNY, which was founded 240 years ago.In this episode, Leigh-Ann is opening up her leadership playbook and sharing her perspectives on how to lead through chaos with clarity, why coherence is her defining word for today’s AI era, and how organizations can balance trust, innovation, and transformation at scale. Connect with Leigh-AnnBNY Tune in for expert advi...

This episode we’re sitting down with Sanjay Shringarpure, CIO at The Freeman Company, to unpack the intangibles of leadership. These are the qualities you can’t easily measure on a dashboard but are often the key difference between leaders who talk about transformation and those who actually achieve it.Over his two decades of technology leadership experience, Sanjay has built a strong track record of leading major digital transformation projects by drawing on his ability to foster collaboration while delivering innovative solutions. From decision velocity to creating a culture of extreme transparency, he has mastered the inta...

There is no better guest to celebrate our 100th Whisperers episode with than Denise Russell Fleming, CIO and EVP of Technology & Global Services at BD. Denise has built a remarkable career across telecom, aerospace, defense, and healthcare, leading large-scale transformation while staying laser-focused on three vital areas: purpose, people, and impact. Throughout her leadership journey, her ability to ensure clarity and deliver outcomes at scale has made her the go-to for orchestrating the most complex cross-company, high-stakes initiatives.Denise embodies everything it means to be a Tech Whisperer. In this episode, we’re unpacking her playbook, the ex...

What does it take to lead technology at enterprise scale in a world defined by AI, ambiguity, and nonstop disruption?That’s one of the big questions we’re exploring in this episode with guest Mojgan Lefebvre, EVP and Chief Technology & Operations Officer at Travelers. Since joining the property casualty insurer in 2018, Mojgan has been the driving force behind its digital and operational transformations, modernizing core platforms, strengthening customer experience, and enabling business growth through technology.Mojgan’s professional journey spans senior leadership roles across insurance, healthcare, consulting, and technology, with a perspective that’s been inf...

There are leaders who understand technology, and there are leaders who understand people, but when someone comes along who truly masters both, incredible things start to happen. Shelia Anderson, EVP and Chief Information & Digital Officer at Unum, is one of those rare and special leaders. A four-time CIO and Hall of Fame inductee, Shelia has built a career defined by transformation, resilience, and developing others. In this episode, we are unpacking Shelia’s playbook to learn about: Leading enterprise-scale transformationsRecognizing when it’s time to step into a new environmentLeading human-centered AI integrationAttracting and retaining top tale...

In this episode, we are sitting down with Keith Ferrazzi, bestselling author of Never Eat Alone and Never Lead Alone, to talk about what leadership, teamship, and trust really look like in an AI-driven world, and how to strengthen relationships by embracing candor.Drawing on his research and insights as well as strategies and tools from his books, Keith is opening up his playbook to share how leaders can stop thinking about AI in silos. We’ll explore the secrets to growing meaningful professional relationships, building high-performing teams, and leading in today’s dynamic and interconnected business envi...

In this episode, we are shining the light on a leader whose journey truly plays out like a movie. Sastry Durvasula has one of those rare stories that blends technical mastery, human-centered leadership, and bold reinvention. After starting out as an engineer, his career journey has included leading transformation for a number of big brand organizationizations. He’s now the Chief Operating, Information, and Digital Officer at TIAA, a $1.4 trillion, 100+ year-old financial institution. From film knowledge to navigating AI, uncertainty, and large-scale change, Sastry’s expertise knows no bounds, and now, you’re getting a front-row seat to tap into a...

In this era of accelerated disruption, leaders who have the right combination of clarity, courage, and conviction stand apart from the pack. GSK Chief Digital & Technology Officer Shobie Ramakrishnan brings all of that to the table—and then some! With her deep and broad experience in both biotech and hi-tech companies, Shobie has mastered the art of leading at scale, engaging the whole organization in digital transformation, and positioning herself to embrace what the future will bring. As Shobie shows us, the most successful leaders do more than keep up; they play offense. Join us as we unp...

After years of interviews with dozens of incredible digital leaders, we’ve explored countless “answer the call” moments, and as we’ve seen, great leaders don’t rely on luck to receive those calls. They place themselves in the right place at the right time so that when the time comes, they are at the top of the list. Jeanine Charlton, the Chief Technology & Digital Officer at Merchants Fleet, is a perfect example of such a leader. In this episode, we are unpacking Jeanine’s customer-first, business-first executive playbook, which has included having responsibility for a $2 billion P&L and 3,500...

This week, we are shining a light on Mike Anderson, Chief Digital & Information Officer at Netskope, to unpack the mindset and playbook behind his exceptional ability to “lift as he climbs.” Mike’s not your typical tech exec; he’s a business guy in an IT wrapper, someone who’s as comfortable in the boardroom as he is in the scrum room. From his early days at Schneider Electric to helping Netskope go public, Mike shares hard-earned lessons on balancing transformation with operational excellence, reshaping pressure into performance, and leveraging storytelling as a leadership superpower.Tune in for...

This week, we are shining the light on one of the most intentional and inspiring CIOs in the game, Ken Piddington, Chief Digital, Technology, & Integration Officer at RelaDyne. Ken exemplifies what it means to be a leader who teaches, mentors, and communicates with purpose. Over the years, we’ve collected several of his “Ken-isms,” the short, punchy expressions that encompass his leadership philosophy, strategy, and core beliefs. In this episode, we’ll explore these pillars of his leadership playbook and dig into how he uses teaching in his leadership approach, giving you new insights on how to lead tra...

Mindy Simon’s path from a Nebraska farm to her current role as Chief Operating Officer of Aon, where she helms a 22,000-person global operation, is anything but conventional—and that's exactly what makes her story so compelling. Mindy’s a great example of how embracing your roots can empower your future, and in this episode, we are shining a light on why she is the kind of transformational leader everyone wants on their team. We’re unpacking Mindy’s transformational leadership playbook, which is built around a people-first mindset, a sharp focus on measurable outcomes, and a rare calm...

In this episode we’re shining the light on the leadership superpowers and industry impact of Diane Schwarz, Group CIO of Smurfit Westrock, a global leader in sustainable packaging. Diane’s leadership style is a unique blend of calm confidence, strategic clarity, and operational excellence that turns traditional roles inside out. You’ll hear why those around her refer to her not just as a CIO but as a Chief Integration Officer, Chief Inspiration Officer, Chief Innovation Officer, and more.We will unpack how Diane masterfully led the IT integration of two global giants, and we’ll dig into...

In this episode of Tech Whisperers, we are joined by two experts who are shaping the future of AI in the enterprise, Dr. Lisa Palmer, CEO of Dr. Lisa AI, and Ashwin Rangan, CEO at DoubleCheck Solutions. Lisa and Ash are sharing a wealth of practical, actionable insights to help us uncover why AI initiatives stall out at the “messy middle” and what leaders can do to reignite progress and start generating real business value. Not only have both Lisa and Ashwin walked in the shoes of a CIO, they are also the authors of new books that...