Tech Whisperers: Inside the Playbooks of the Best Digital Leaders

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

Join futurist Bob Johansen, foresight expert Gabe Cervantes, and generative software innovator Jeremy Kirshbaum as they explore how generative AI is reshaping leadership. They discuss essential skills for CIOs, including 'future back' thinking and the shift from VUCA to BANI. Discover how to ethically embrace AI while fostering human-centric leadership, and learn how resilience and emotional intelligence are key in this rapidly evolving landscape. Get ready for insights that promise to transform your approach to 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

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

This episode we’re shining the light on Kathy Kay, a leader whose name is synonymous with “building” — and she is a builder in every sense of the word. Kathy not only excels at developing high-performance teams, she extends that builder mindset across multiple areas in both her personal and professional lives.In a wide-ranging conversation, Kathy is sharing how she applies her philosophy of building to her current role as EVP & CIO at Principal Financial Group. We’ll explore her strengths in building courage, collaboration, community, innovation, and family as she lives out a leadership style that balances personal and professional success.Tune in to learn:How to simplify complex projects for your teamHow to ensure your team is aligned with the overall corporate strategyHow to maintain optimism and keep your team energizedKathy’s plans for using AI and cloud innovation to enable business growthKathy’s insights about the human impact of AIAnd more!Featuring submitted questions from:Dan Houston, Chairman & CEO (Ret.), Principal Financial GroupAnil Cheriyan, Board Member & 3x CIO, Tech Whisperers Guest Ep. 55Ryan Downing, CIO, Enterprise Business Solutions, Principal Financial GroupJen Hartsock, Chief Information & Digital Officer, CargillRajesh Arora, Chief Data & Analytics Officer, Principal Financial GroupLance Henning, Chief Executive Officer, Greater Des Moines Habitat for HumanityBrian Waller, President, Technology Association of IowaMackenzie Keogh, Kathy’s DaughterJackson Keogh, Kathy's 2-Year Old Grandson

Inducted in the CIO Hall of Fame in 2019, Zack Hicks is a leader who has left a major impact on the CIO profession through his relentless pursuit of innovation to drive new business outcomes. Having previously been the CEO of Toyota Connected and the Chief Digital Officer at Toyota Motor North America, Zack is now making his mark at Kimberly-Clark as their Chief Digital & Technology Officer.With a career that includes numerous “answer-the-call” moments, Zack knows what it takes for leaders to deliver major wins for their organizations. In this episode, we’re unpacking some of those key moments that have defined Zack’s career and set him apart as a true industry innovator and disruptor.Tune in to learn:What led Zack to join Kimberly-Clark after 26 years with ToyotaHow Zack approaches his role at Kimberly-ClarkHow Zack overcame a variety of challenges at Toyota early in his careerThe key to balancing people and technology amid the rise of AI The skills tech leaders need in order to build trust in a digital transformation journeyFeaturing submitted questions from:Brian Kursar, Group VP & Head of Enterprise AI, Toyota Motor North AmericaBarbara Cooper, Retired CIOGreg Beckwith, Director & Chief of Staff, Kimberly-ClarkTeresa Miquelarena, VP, Global Information & Digital Strategy, Kimberly-ClarkDeena Dayalan, Head of Digital Operations in Bangalore, Kimberly-Clark

While many CIOs are busy figuring out what the CIO’s role looks like today, our guest this week is already answering the question, “What does the CIO of tomorrow look like?” As EVP and Chief Information, Digital, and Corporate Strategy Officer at Tractor Supply Co., Rob Mills has been instrumental in driving the $14.6 billion retailer’s rapid growth, profitability, and world class customer experience. His influence and impact are expansive: He has a hand in P&L, serves on Tractor Supply’s executive committee, and also sits on numerous public and private boards.Join us as we talk tech, digital, and strategy with Rob and learn about:The evolution of the CIO’s roleHow to lead through digital transformationHow Tractor Supply handles customer experience and store supportHow tech leaders can balance speed and accuracyThe differences between empowerment and delegation and how to balance bothFeaturing submitted questions from:Mike Seals, Chief Digital Officer & SVP of Strategy, Hussman CorporationChris Colla, Chief Technology Officer, B&G FoodsHal Lawton, President & CEO, Tractor Supply Co.Joy Brown, SVP & CDO, Boston Medical Center, Board Director, Tractor Supply Co.Brandon Jacobson, VP of Corporate Strategy, Tractor Supply Co.

There are some Tech Whisperers who leave a legacy by investing their skills in just one or two companies across their career, and then there are those who leave their legacy by making their mark on several organizations throughout their career. As a whopping seven-time CIO and a three-time winner of the CIO100 Award, Mark Settle is a standout example of the latter. During his CIO journey, Mark somehow also made the time to publish two must-read books, Truth from the Valley, A Practical Primer on IT Management for the Next Decade and Truth from the Trenches: A Practical Guide to the Art of IT Management.As an expert truth teller, startup adviser, and advisory board member, Mark has mastered the art of helping teams and businesses cut through the fluff to focus on what matters most. In this episode, he’s sharing some of his secret sauce with us.Join us as we unpack Mark’s leadership playbook to learn:How to handle curveballs under pressureHow to effectively utilize discretionary bandwidthHow to navigate organizational politicsStrategies for a CIO’s first 90 daysThe key to becoming a Level 5 leaderFeaturing submitted questions from:Ralph Loura, Hall of Fame CIO & Chairman of the Board, SustainableIT.orgJulie Cullivan, Board Director, Former Chief Technology & People OfficerCarter Busse, CIO, WorkatoAlvina Antar, Advisor, Board Member, & Former CIO

You’re in for a special treat with this episode as we sit down with the GOAT, the greatest-of-all-time CIO, Robert B. Carter. Rob served as the CIO of FedEx for almost a quarter of a century, during which time he transformed IT strategy and led the company to unprecedented success, not to mention 27 straight CIO 100 Awards.In this episode, we’re delving into Rob’s extraordinary 24-year tenure at FedEx and exploring the essence of leadership, the importance of humility, the role of mentorship, and the challenges and milestones that have defined his remarkable career.Join us as we unpack Rob’s expansive digital leadership playbook to learn:How Rob kept himself energized at FedEx for such a long durationHow mentors impacted his careerWhat it takes to be a successful technology executiveHow effective leaders balance personal and professional priorities A peak into what Rob has planned next!Featuring submitted questions from:Charlie Feld, CEO & Founder, Feld Group InstituteRachel Harvey, Rob Carter’s Executive Assistant for 31 years Ken Spangler, Co-Founder, AdaptiveIONDottie Berry, Chief of Staff to Rob CarterMike Glenn, EVP Market Development & Corp Communications (ret.), FedExChris Winton, SVP HR, Comcast; Board Member, Methodist Le Bonheur Healthcare

As the leader of over 5,000 technologists, Monica Caldes, Global CIO at Liberty Mutual Insurance, has established herself as one of the top digital executives in the industry. She is one of those rare leaders that has figured out the secret formula for mixing boldness, courage, empathy, and kindness, making her a leader that people are eager to work under.In this episode, we are shining the light onto Monica’s story to uncover the “It Factor” that makes her such an incredible leader, and we’ve included some really cool surprises for Monica along the way!Join us as we unpack Monica’s digital leadership playbook to learn:How a strong CEO/CIO partnership creates new opportunities and enables fast transformationHow Monica develops future-ready cultures and teamsHow to effectively lead with thousands of team members under your authorityHow to properly apply adaptability in your leadershipHow to embrace and learn from major mistakesFeaturing submitted questions from:Jim MachPhee, COO at Liberty Mutual InsuranceJim Fowler, CTO at NationwideAndrew Palmer, SVP & CIO at Liberty Mutual InsuranceKyle Benton (We don’t want to spoil who this is!)