Tech Whisperers: Inside the Playbooks of the Best Digital Leaders

Ouellette & Associates
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Mar 18, 2026 • 54min

Denise Russell Fleming: Leading with Trust at Enterprise Scale

There is no better guest to celebrate our 100th Whisperers episode with than Denise Russell Fleming, CIO and EVP of Technology & Global Services at BD. Denise has built a remarkable career across telecom, aerospace, defense, and healthcare, leading large-scale transformation while staying laser-focused on three vital areas: purpose, people, and impact. Throughout her leadership journey, her ability to ensure clarity and deliver outcomes at scale has made her the go-to for orchestrating the most complex cross-company, high-stakes initiatives.Denise embodies everything it means to be a Tech Whisperer. In this episode, we’re unpacking her playbook, the experiences that shaped her career, and the lessons she’s learned—and that you can apply—from navigating complex transformations.Connect with Denise: https://www.linkedin.com/in/deniserussellfleming/BD: https://www.bd.com/Tune in for wisdom from Denise’s journey, including:Balancing executive responsibilities, community engagement, and personal growthThe key to wearing multiple leadership hats simultaneouslyFinding alignment between enterprise strategy and IT investmentLeading enterprise-scale transformation in highly regulated areasFeaturing submitted questions from:Ted Colbert, Former President & CEO, Boeing Defense, Space, & SecurityLarry Quinlan, 11x Board Director, Former CIO, Whisperers Guest - Episode 7Michael Bennett, Board Member, Former CIODani Brown, EVP & CIO, Whirlpool, 3x Board Director, Episode 4 Whisperers Guest Hermes Vallejo, VP of IT, Medical Segment NA, Marketing, R&D RAQA, BDRona Bunn, CIO, NACD (National Assoc of Corp Directors), Episode 32 GuestSabina Ewing, CIO, Business & Technology Services, Abbott, Episode 11 GuestTony Ezell, President of the Americas & Chief Marketing Officer, BDBharat Amin, 4x Board Member, Former CIOEarl Newsome, CIO, Cummins, Episode 71 Guest
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8 snips
Feb 25, 2026 • 59min

What Transformative CTOs Do Differently: Mojgan Lefebvre on Leading in the Age of AI

What does it take to lead technology at enterprise scale in a world defined by AI, ambiguity, and nonstop disruption?That’s one of the big questions we’re exploring in this episode with guest Mojgan Lefebvre, EVP and Chief Technology & Operations Officer at Travelers. Since joining the property casualty insurer in 2018, Mojgan has been the driving force behind its digital and operational transformations, modernizing core platforms, strengthening customer experience, and enabling business growth through technology.Mojgan’s professional journey spans senior leadership roles across insurance, healthcare, consulting, and technology, with a perspective that’s been informed and expanded by her board experience and her passion for developing future-ready talent. From leaving Iran at 19 to leading a 15,000-person global tech and ops organization, she shares how her leadership philosophies were forged long before she ever held a title and why a human-centered approach to AI is the way forward.Connect with Mojgan: https://www.linkedin.com/in/mojganlefebvreTravelers: https://www.travelers.com/Tune in for practical insights from Mojgan’s playbook, including:The keys to fast execution at enterprise scaleLeadership skills necessary for leading enterprise transformationHow to balance innovation with optimizationUsing technology to improve customer experienceThe mindset and skillset for leading during transformationFeaturing submitted questions from:Shelia Anderson, EVP, Chief Information & Digital Officer, Unum, Episode 87 GuestMarc Wood, CIO, Berkshire Hathaway SpecialtyJason Galvin, SVP & CIO, Personal Insurance, TravelersKamalesh Dwivedi, President & Partner, 3LinesChristine Kalla, EVP & General Counsel, TravelersAndreas Wetterwald, Chief Data & Analytics Officer, TravelersKevin De Sa, SVP & CIO, Business Insurance, TravelersJames McGlennon, EVP & Global CIO, Liberty Mutual (ret)
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Feb 4, 2026 • 48min

Proven Beyond a Reasonable Doubt: The Hall of Fame Career of Shelia Anderson

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 transformationsRecognizing when it’s time to step into a new environmentLeading human-centered AI integrationAttracting and retaining top talentBeing a leader people want to follow even—and especially—in moments of high accountabilityFeaturing submitted questions from:James McGlennon, EVP & Chief Information Officer (Ret.), Liberty MutualMojgan Lefebvre, VP & Chief Technology & Operations Officer, TravelersMatt Keane, VP Data Science & AI, Enterprise Value Stream Builder, Head of InnovationKelley Kage, SVP & Chief Information Officer, Employers InsuranceAndrew Walker, Chief Customer Operations Officer, Unum Group
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Jan 14, 2026 • 60min

Keith Ferrazzi on Architecting the Future of Human-AI Collaboration

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 eraThe importance of candor and collaborationThe power of asking the right questionsBuilding and strengthening leadership relationshipsFeaturing submitted questions from:Deepa Soni, CIO, New York Life, Episode 40 GuestLeigh-Ann Russell, CIO & Global Head of Engineering, BNYFrank Congiu, EVP for Human Capital Strategy & Executive Partnerships, Randstad Enterprises Stephanie Kramar, CHRO, L’OréalLisa Buckingham, Global Chief People & Culture Officer, Vialto Partners
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Dec 17, 2025 • 59min

How TIAA’s Sastry Durvasula Leads Transformation, One Reinvention at a Time

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 onceHow he uses reinvention as a superpowerHow to know when transformation has turned the cornerNavigating decision-making in the fog of uncertainty and leading with convictionFeaturing submitted questions from:Sathish Muthukrishnan, Chief Information, Data, & Digital Officer, Ally, Episode 50 GuestEileen Lash, Chief Administrative Officer, TIAANeal Sample, Chief Digital & Technology Officer, Best BuySwatee Singh, CIO for Data, AI, & Corporate Technology, TIAAYogs Jayapraksam, Chief Technology & Digital Officer, Deluxe
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Dec 3, 2025 • 56min

The Speed of Reimagination: How Shobie Ramakrishnan Leads Change That Lasts

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 speedHow to engage the entire organization in digital transformationThe importance of “white space” for innovationShobie’s approach to talent strategy and development at GSKStrategies for success in the next decadeFeaturing submitted questions from:Diane Schwarz, Group CIO, Smurfit Westrock, Episode 79 GuestKarenann Terrell, Board Director, Technology Advisor, Former CDTO, Episode 48 GuestAdam Uphadyay, SVP & CDTO, Vertex PharmaceuticalsDeborah Waterhouse, CEO, ViiV Healthcare, President of Global Health, GSK
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Nov 19, 2025 • 55min

Setting Yourself up to Get the Call: Jeanine Charlton’s Leadership Playbook

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 chaosWhat has anchored Jeanine throughout her careerThe key skills and traits that have helped Jeanine achieve sustained successJeanine’s most important advice for women entering tech industriesFeaturing submitted questions from:Ralph Szygenda, Industry Executive & Advisor (Ret.), 2007 CIO Hall of FameKevin Torgerson, Independent Board Director & AdvisorAndi Karaboutis, Board Director of Aon, Perrigo, Savills, Autoliv, Advisory Board of  Decagon, iGreenTree.aiKurt Taylor, VP, Client Solutions, Merchants FleetChethana Halasinahalli, Sr Manager IT Applications at ONEOK, Graduate of TechLX Leadership ProgramSamantha Charlton, Entrepreneur, Gym Owner, Personal Trainer
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Nov 5, 2025 • 55min

Netskope CIO Mike Anderson on Future Proofing Your Team & Career

This week, we are shining a light on Mike Anderson, Chief Digital & Information Officer at Netskope, to unpack the mindset and playbook behind his exceptional ability to “lift as he climbs.” Mike’s not your typical tech exec; he’s a business guy in an IT wrapper, someone who’s as comfortable in the boardroom as he is in the scrum room. From his early days at Schneider Electric to helping Netskope go public, Mike shares hard-earned lessons on balancing transformation with operational excellence, reshaping pressure into performance, and leveraging storytelling as a leadership superpower.Tune in for insights from Mike’s playbook, including:The importance of learning the business in your first 90 daysInstilling ambition and helping people aspire to moreSecuring buy-in for bold ideasHow he approaches his dual role leading Netskope’s strategy office and ITLearning from adversity and staying positiveFeaturing submitted questions from:Annette Clayton, Board Director, OshKosh, Nordson, Flash, NXP Semiconductors, & Duke EnergyAmanda Anderson, Senior Director, Integrated Marketing, Digital & Marketing Ops, NetskopeClint Clark, VP, IT Engineering & Architecture, NetskopeDanyel Bischof-Forsyth, Chief Technology & Information Officer, 7 Brew Coffee, Episode #73 GuestAlan Rankin, Mike’s Long Time Friend
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Oct 22, 2025 • 1h

CIO as Teacher: Inside Ken Piddington’s Leadership Excellence Playbook

This week, we are shining the light on one of the most intentional and inspiring CIOs in the game, Ken Piddington, Chief Digital, Technology, & Integration Officer at RelaDyne. Ken exemplifies what it means to be a leader who teaches, mentors, and communicates with purpose. Over the years, we’ve collected several of his “Ken-isms,” the short, punchy expressions that encompass his leadership philosophy, strategy, and core beliefs. In this episode, we’ll explore these pillars of his leadership playbook and dig into how he uses teaching in his leadership approach, giving you new insights on how to lead transformational change successfully for your organization as well as your people.Tune in for insights from Ken’s career, including:How to balance business results and team development“Anchor the Why”: Ken’s approach to vision and purposeThe relationship between execution and speedCharacter consistency and being the thermostat instead of the thermometerFeaturing submitted questions from:Mohammed ShareefKath Marston, Executive Director, Technology PartnersAlex Pore, Senior Director, Business Integration, RelaDyneStephen Webster, President, CEO, Founder, SIS Holdings Group
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Oct 8, 2025 • 40min

How Mindy Simon Guides Aon Through Transformation with Calm & Clarity

Mindy Simon’s path from a Nebraska farm to her current role as Chief Operating Officer of Aon, where she helms a 22,000-person global operation, is anything but conventional—and that's exactly what makes her story so compelling. Mindy’s a great example of how embracing your roots can empower your future, and in this episode, we are shining a light on why she is the kind of transformational leader everyone wants on their team. We’re unpacking Mindy’s transformational leadership playbook, which is built around a people-first mindset, a sharp focus on measurable outcomes, and a rare calmness under pressure. We’ll also explore how she has successfully led in finance, IT, and operations across multiple industries; how she ties technology to business growth; and what it takes to truly deliver value in a fast-moving, data-rich world. Check out Mindy’s Investor Day talk (Jump to 02:17:25 in the video) Tune in for valuable learnings from Mindy’s career, including:Early startup lessons and transformation at ConAgraTying IT investments to measurable business outcomesHow Aon is embedding AI across the client journeyHow and why Mindy applies a people-first mindset to leadingWhy disrupting yourself is better than being disruptedFeaturing submitted questions from:Steve Zerby, Award-Winning CIO, Advisor, Guest for Episode 17Annie Baymiller, CIO, Owens Corning, Guest for Episode 17Greg Case, Chief Executive Officer, AonAndi Karaboutis, 4x Board Director, 3x CIO, Guest for Episode 68

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