Tech Whisperers: Inside the Playbooks of the Best Digital Leaders

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 transformations
Recognizing when it’s time to step into a new environment
Leading human-centered AI integration
Attracting and retaining top talent
Being a leader people want to follow even—and especially—in moments of high accountability

Featuring submitted questions from:
James McGlennon, EVP & Chief Information Officer (Ret.), Liberty Mutual
Mojgan Lefebvre, VP & Chief Technology & Operations Officer, Travelers
Matt Keane, VP Data Science & AI, Enterprise Value Stream Builder, Head of Innovation
Kelley Kage, SVP & Chief Information Officer, Employers Insurance
Andrew Walker, Chief Customer Operations Officer, Unum Group

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 environment.
Connect with Keith: https://www.linkedin.com/in/keithferrazzi/
Ferrazzi Greenlight: https://ferrazzigreenlight.com/
Never Eat Alone: https://a.co/d/cOdJlPx (Amazon Link)
Never Lead Alone: https://a.co/d/0ZFWB3a (Amazon Link)

Tune in for expert wisdom from Keith, including:
How to build high-performing teams in the AI era
The importance of candor and collaboration
The power of asking the right questions
Building and strengthening leadership relationships

Featuring submitted questions from:
Deepa Soni, CIO, New York Life, Episode 40 Guest
Leigh-Ann Russell, CIO & Global Head of Engineering, BNY
Frank Congiu, EVP for Human Capital Strategy & Executive Partnerships, Randstad Enterprises
Stephanie Kramar, CHRO, L’Oréal
Lisa Buckingham, Global Chief People & Culture Officer, Vialto Partners

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 all of that leadership knowledge and insight.
Tune in for expert advice from Sastry’s playbook, including:
The challenge of solving yesterday, today, and tomorrow all at once
How he uses reinvention as a superpower
How to know when transformation has turned the corner
Navigating decision-making in the fog of uncertainty and leading with conviction

Featuring submitted questions from:
Sathish Muthukrishnan, Chief Information, Data, & Digital Officer, Ally, Episode 50 Guest
Eileen Lash, Chief Administrative Officer, TIAA
Neal Sample, Chief Digital & Technology Officer, Best Buy
Swatee Singh, CIO for Data, AI, & Corporate Technology, TIAA
Yogs Jayapraksam, Chief Technology & Digital Officer, Deluxe

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 unpack her leadership playbook and explore how to show up with purpose, navigate complexity with curiosity, and harness this era of rapid disruption to set our organizations up to thrive.
Tune in for tips from Shobie’s playbook, including:
How to build organizational agility and speed
How to engage the entire organization in digital transformation
The importance of “white space” for innovation
Shobie’s approach to talent strategy and development at GSK
Strategies for success in the next decade

Featuring submitted questions from:
Diane Schwarz, Group CIO, Smurfit Westrock, Episode 79 Guest
Karenann Terrell, Board Director, Technology Advisor, Former CDTO, Episode 48 Guest
Adam Uphadyay, SVP & CDTO, Vertex Pharmaceuticals
Deborah Waterhouse, CEO, ViiV Healthcare, President of Global Health, GSK

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 people. We’ll explore the power of resilience, the discipline of operational excellence, and the value of mentorship and clear communication in leadership.
Tune in for valuable learnings from Jeanine, including:
How to lead in high-stakes, high-stress situations with limited time
How to communicate with clarity and calmness amid chaos
What has anchored Jeanine throughout her career
The key skills and traits that have helped Jeanine achieve sustained success
Jeanine’s most important advice for women entering tech industries

Featuring submitted questions from:
Ralph Szygenda, Industry Executive & Advisor (Ret.), 2007 CIO Hall of Fame
Kevin Torgerson, Independent Board Director & Advisor
Andi Karaboutis, Board Director of Aon, Perrigo, Savills, Autoliv, Advisory Board of Decagon, iGreenTree.ai
Kurt Taylor, VP, Client Solutions, Merchants Fleet
Chethana Halasinahalli, Sr Manager IT Applications at ONEOK, Graduate of TechLX Leadership Program
Samantha Charlton, Entrepreneur, Gym Owner, Personal Trainer