Tech Whisperers: Inside the Playbooks of the Best Digital Leaders

Ouellette & Associates
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  • BUSINESS
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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!

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

    5D AGO

    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/mojganlefebvre Travelers: 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 transformation Featuring 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)

    59 min

  2. FEB 4

    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 accountability Featuring 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

    48 min
  3. Keith Ferrazzi on Architecting the Future of Human-AI Collaboration

    JAN 14

    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 relationships Featuring 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

    1 hr
  4. How TIAA’s Sastry Durvasula Leads Transformation, One Reinvention at a Time

    12/17/2025

    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 conviction Featuring 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

    59 min
  5. The Speed of Reimagination: How Shobie Ramakrishnan Leads Change That Lasts

    12/03/2025

    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 decade Featuring 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

    56 min
  6. Setting Yourself up to Get the Call: Jeanine Charlton’s Leadership Playbook

    11/19/2025

    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 industries Featuring 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

    55 min
  7. Netskope CIO Mike Anderson on Future Proofing Your Team & Career

    11/05/2025

    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 positive Featuring 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

    55 min
  8. CIO as Teacher: Inside Ken Piddington’s Leadership Excellence Playbook

    10/22/2025

    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 thermometer Featuring submitted questions from: Mohammed ShareefKath Marston, Executive Director, Technology PartnersAlex Pore, Senior Director, Business Integration, RelaDyneStephen Webster, President, CEO, Founder, SIS Holdings Group

    1 hr
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About

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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