Tech Whisperers: Inside the Playbooks of the Best Digital Leaders

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 thinking
• How to augment your leadership style
• The industry’s transition from “VUCA” to “BANI” (Brittle, Anxious, Nonlinear, and Incomprehensible)
• Opportunities the GenAI era presents to rehumanize leadership
• How to embrace AI ethically while maintaining human-centric leadership

You 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, PPG
• Will Markow, SVP of Workforce Solutions, CyberWarrior.com
• Martha Heller, CEO, Heller Search Associates

 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 ready
• Amy’s advice on developing your skills as a public speaker
• The importance of maintaining a continuous learning mindset
• Amy’s lessons learned from experiences early in her career

Featuring submitted questions from:

• Marc Gordon, Senior Advisor, Boston Consulting Group
• Keith Silvestri, Chief Technology Officer, KeyBank
• Mike Onders, EVP & CIO, KeyBank
• Stan Brady, Amy’s Husband
• Jim Merlino, MD, EVP & Chief Innovation Officer, The Joint Commission
• Caroline 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 leadership
• How to bounce back from failure
• The power of storytelling
• How Nationwide has built and maintained a high-performing technology organization
• The personal hobby Jim applies to recognize outstanding team members

Featuring submitted questions from:

• Monica Caldas, EVP & Global Chief Information Officer, Liberty Mutual Insurance & Tech Whisperers Guest Ep. 59
• Ehren Powell, Chief Digital Officer, Marathon Petroleum
• David Burns, Chief Information Officer, GE Aerospace
• Angelica Tritzo, CIO & EVP Digital Technologies, GE Vernova
• Misty Kuamoo CIO of Corporate Technology, Nationwide
• Caroline Eberle, Garter Business Development Executive
• Joey 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 team
• How to ensure your team is aligned with the overall corporate strategy
• How to maintain optimism and keep your team energized
• Kathy’s plans for using AI and cloud innovation to enable business growth
• Kathy’s insights about the human impact of AI
• And more!

Featuring submitted questions from:

• Dan Houston, Chairman & CEO (Ret.), Principal Financial Group
• Anil Cheriyan, Board Member & 3x CIO, Tech Whisperers Guest Ep. 55
• Ryan Downing, CIO, Enterprise Business Solutions, Principal Financial Group
• Jen Hartsock, Chief Information & Digital Officer, Cargill
• Rajesh Arora, Chief Data & Analytics Officer, Principal Financial Group
• Lance Henning, Chief Executive Officer, Greater Des Moines Habitat for Humanity
• Brian Waller, President, Technology Association of Iowa
• Mackenzie Keogh, Kathy’s Daughter
• Jackson 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 Toyota
• How Zack approaches his role at Kimberly-Clark
• How Zack overcame a variety of challenges at Toyota early in his career
• The 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 journey

Featuring submitted questions from:

• Brian Kursar, Group VP & Head of Enterprise AI, Toyota Motor North America
• Barbara Cooper, Retired CIO
• Greg Beckwith, Director & Chief of Staff, Kimberly-Clark
• Teresa Miquelarena, VP, Global Information & Digital Strategy, Kimberly-Clark
• Deena 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 role
• How to lead through digital transformation
• How Tractor Supply handles customer experience and store support
• How tech leaders can balance speed and accuracy
• The differences between empowerment and delegation and how to balance both

Featuring submitted questions from:

• Mike Seals, Chief Digital Officer & SVP of Strategy, Hussman Corporation
• Chris Colla, Chief Technology Officer, B&G Foods
• Hal 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 pressure
• How to effectively utilize discretionary bandwidth
• How to navigate organizational politics
• Strategies for a CIO’s first 90 days
• The key to becoming a Level 5 leader

Featuring submitted questions from:

• Ralph Loura, Hall of Fame CIO & Chairman of the Board, SustainableIT.org
• Julie Cullivan, Board Director, Former Chief Technology & People Officer
• Carter Busse, CIO, Workato
• Alvina 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 duration
• How mentors impacted his career
• What it takes to be a successful technology executive
• How 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 Institute
• Rachel Harvey, Rob Carter’s Executive Assistant for 31 years 
• Ken Spangler, Co-Founder, AdaptiveION
• Dottie Berry, Chief of Staff to Rob Carter
• Mike Glenn, EVP Market Development & Corp Communications (ret.), FedEx
• Chris 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 transformation
• How Monica develops future-ready cultures and teams
• How to effectively lead with thousands of team members under your authority
• How to properly apply adaptability in your leadership
• How to embrace and learn from major mistakes

Featuring submitted questions from:

• Jim MachPhee, COO at Liberty Mutual Insurance
• Jim Fowler, CTO at Nationwide
• Andrew Palmer, SVP & CIO at Liberty Mutual Insurance
• Kyle Benton (We don’t want to spoil who this is!)

In this episode, we are shining the light on Dr. Janet Sherlock, a digital and retail executive who leads through her expertise in digital transformation, customer experience, omnichannel strategy, data, and AI and machine learning. 

Janet’s career spans companies such as ExxonMobile, British Petroleum, and, for the last seven years, Ralph Lauren, where she served as Chief Digital & Technology Officer, driving the company’s digital transformation strategy and leading their global e-commerce strategy. 

Join us as we unpack Janet’s digital leadership playbook to learn:

• How to lead your team through complex goals while remaining a leader people want to be around
• How to maintain the CIO role’s core identity and purpose and demonstrate it to other executives
• How tech companies can balance strategy and organizational design 
• Why she decided to pursue her EdD and how her research has impacted her career and perspectives
• How to use structure to enable results

Featuring submitted questions from:

• Karenann Terrell, Technology Advisor, Former Chief Digital & Technology Officer
• Anil Cheriyan, Former CIO/CTO
• Michael Smith, Chief Information Officer at Estee Lauder
• Earl Newsome, Chief Information Officer at Cummins Inc.
• Kim Saxton, Chief Executive Officer at TechPACT