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Tech Whisperers: Inside the Playbooks of the Best Digital Leaders

Ouellette & Associates
Tech Whisperers: Inside the Playbooks of the Best Digital Leaders
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  • Monte Ford: The Evolution from Executive to Boardroom Strategist
    In this episode, we are sitting down with a very special guest who has had a massive impact on the CIO profession–Monte Ford. Monte is a CIO Hall of Fame inductee, an advisor to many of the top CIOs and business leaders, and a board member for several large companies, such as JetBlue and Centene. For all of his accolades and accomplishments, Monte is a leader who prefers to keep a low profile, so it was a thrill to have the opportunity to sit down with him and unpack his leadership playbook. Monte is opening up about his career journey, his transition into the board room, what he has learned serving on boards, and more. Listen in to discover some of the many reasons Fortune Magazine named him one of the 50 smartest people in technology.Join us as Monte shares his insights on:The evolving influence of corporate tech leadersThe traits that separate great CIOs apartThe leadership qualities that are most important in a digital-first environmentHow he builds and maintains a strong relationship networkHow he weaves forward-thinking into his leadership approachFeaturing submitted questions from:Rob Carter, FedEx CIO (ret), Board Director, Episode 60 GuestJim Fowler, CIO, Nationwide, Episode 65 GuestKathy Kay, CIO, Principal Financial Group, Episode 64 GuestJohn Repko, 5x CIO, Board Member, AdvisorZack Hicks, CIO, Kimberly Clark, Episode 63 GuestMichelle Greene, CIO, Cardinal Health, Board DirectorSabina Ewing, CIO, Abbott
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  • 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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About Tech Whisperers: Inside the Playbooks of the Best Digital Leaders

Tech Whisperers: Inside the Playbooks of the Best Digital Leaders, is a podcast for CxOs and industry leaders looking to hear conversations that unpack the leadership philosophies, decision making thought processes and unique expressions that differentiate the best. If you’re looking to gain an edge, instill new mindsets, and move out of your comfort zone, you’ve found the right community. Welcome to Tech Whisperers!
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