Tech Whisperers: Inside the Playbooks of the Best Digital Leaders

• Tech, Banking, and the Power of Translation: Dan Massey’s Leadership Playbook

  For this episode, we had the privilege of visiting the Regions Bank headquarters in Birmingham, Alabama, for an in-person conversation with Chief Enterprise Operations and Technology Officer Dan Massey. “Digital Dan,” as he’s known to many, embodies what it means to bridge technology, operations, and innovation at the highest level, ensuring technology is not just an enabler but a true driver of business value. He’s someone who is fully present no matter the situation, whether he’s leading a powerhouse organization of 5,000 employees, spending time with his family, or writing and performing music with his band of 30 years, The Shivers.Dan is opening up his leadership playbook to trace how his career journey and experiences have shaped him into the leader he is today.Join us as we explore Dan’s unique ability to translate business and technology, including:How he seamlessly translates between tech, engineering, and business talkHow he manages through conflicting agendas or stakeholdersHow he is navigating digital transformation at RegionsThe value of combining operations and technology in a large organizationDan’s approach to balancing his personal and professional lifeFeaturing submitted questions from:Ken Meyer, CIO of Enterprise Functions Technology, Wells FargoKate Danella, Head of Consumer Bank, Regions BankAnil Cheriyan, 3x CIO, Board Member & AdvisorAmeet Shetty, CDO – US Information Solutions, EquifaxScott Case, Head of Technology & Operations, Prudential FinancialRiley Massey, Dan’s DaughterWill Jones, Media Manager, Band Member

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• The CIO-to-Board Playbook of Hall of Famer Andi Karaboutis

  In this episode, we are shining the light on CIO Hall of Fame legend Adriana (Andi) Karaboutis and some of the incredible milestones that have defined her career—including a 21-year tenure in the automotive industry at Ford and General Motors, followed by technology and business leadership roles at Dell, Biogen, and National Grid. Now, Andi is focused on writing the next chapter in her professional story, serving as a director on four corporate boards.Andi is opening up her leadership playbook to reflect on the challenges she’s overcome, the groundbreaking initiatives she’s led, and her vision for the future. We’ll also explore some of the moments that shaped her into an industry trailblazer.Join us as we discuss key lessons from Andi’s career, including:How to cultivate effective collaboration with C-suite executivesHow a mindset shift on failure helped her build resilienceWhat led to her career transition to DellHow to simplify complex problems and ideasAndi’s “rewirement” approach to retirementFeaturing submitted questions from:Marv Adams, Strategic Advisor, Former CIO/COO/PresidentRalph Szygenda, Former Board Director, CXOJeanine Charlton, CIO, Merchants FleetJustin Mennen, CIO, Shake ShackAlvina Antar, CIO, Zuora & Okta (ret.)Tim Dickson, CIO, Regal RexnordMindy Simon, Global Chief Operating Officer, AON

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• The Augmented CIO: 10 Skills of Game Changing Leadership in the GenAI Era

  With the rise of generative AI, CIOs and IT leaders are experiencing a leadership revolution. GenAI is shaking up both how we engage with technology and how leaders guide their organizations through adoption, governance, and innovation. We are thrilled to have the opportunity to sit down with Institute for the Future’s Bob Johansen and Gabe Cervantes and Handshake’s Jeremy Kirshbaum, whose new book “Leaders Make the Future, Third Edition: 10 New Skills to Humanize Leadership with Generative AI” is out this week. Be among the first to dive into this game-changing resource designed to give leaders clarity on how to lead through this period of rapid digital transformation. Join us as we explore the key themes from the book, including:Future-back vs. present-forward thinkingHow to augment your leadership styleThe industry’s transition from “VUCA” to “BANI” (Brittle, Anxious, Nonlinear, and Incomprehensible)Opportunities the GenAI era presents to rehumanize leadershipHow to embrace AI ethically while maintaining human-centric leadershipYou may remember Bob Johansen from his last visit to the podcast as part of a bonus episode back in 2023. You won't want to miss his latest future-focused insights!Featuring submitted questions from:Dr. Lisa Palmer, CEO, Dr Lisa AI,Bhaskar Ramachandran, VP of IT, CIO, PPGWill Markow, SVP of Workforce Solutions, CyberWarrior.comMartha Heller, CEO, Heller Search Associates

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• Empowering Teammates and Building Tomorrow’s Digital Workforce: Amy Brady’s Tech, Banking & Community Leadership

   In this episode, we are featuring an extraordinary leader who's been blazing trails and inspiring countless others throughout her career. Amy Brady is the Chief Information Officer at KeyBank, where she leads the company's technology, operations, and services organizations.Amy is the epitome of a leader who can seemingly do it all, and because of that she is making her mark across the industry while continually championing causes that uplift women in tech. We're diving into Amy's incredible career journey, uncovering her leadership philosophies, and highlighting those career-defining moments and superpowers that make her so special and impactful. Join us as we explore insights from Amy’s leadership playbook, including:How and why to embrace new roles, even when you don’t feel readyAmy’s advice on developing your skills as a public speakerThe importance of maintaining a continuous learning mindsetAmy’s lessons learned from experiences early in her careerFeaturing submitted questions from:Marc Gordon, Senior Advisor, Boston Consulting GroupKeith Silvestri, Chief Technology Officer, KeyBankMike Onders, EVP & CIO, KeyBankStan Brady, Amy’s HusbandJim Merlino, MD, EVP & Chief Innovation Officer, The Joint CommissionCaroline Eberle, Gartner Business Development Executive

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• Nationwide’s Jim Fowler on the CIO's Good to Great Journey

  One of the hallmarks of a great Chief Technology Officer is that they are able to translate a passion for technology into a driving force for business success. Nationwide’s Jim Fowler is a CTO who does exactly that, by striving for “great” instead of settling for “good.” We are unpacking Jim’s 20+ years of experience across industries, companies, and countries to learn lessons from his career journey and his strengths as a visionary leader that can help CIOs and IT leaders at all levels achieve greatness. Join us as we explore Jim’s leadership playbook and learn:How Jim balances operational excellence with visionary leadershipHow to bounce back from failureThe power of storytellingHow Nationwide has built and maintained a high-performing technology organizationThe personal hobby Jim applies to recognize outstanding team membersFeaturing submitted questions from:Monica Caldas, EVP & Global Chief Information Officer, Liberty Mutual Insurance & Tech Whisperers Guest Ep. 59Ehren Powell, Chief Digital Officer, Marathon PetroleumDavid Burns, Chief Information Officer, GE AerospaceAngelica Tritzo, CIO & EVP Digital Technologies, GE VernovaMisty Kuamoo CIO of Corporate Technology, NationwideCaroline Eberle, Garter Business Development ExecutiveJoey Fowler, Jim’s Daughter

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