Tech Whisperers: Inside the Playbooks of the Best Digital Leaders

Ouellette & Associates

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. Built for Change: Rewiring a 175-Year-Old Company for the AI Era

    May 20

    Built for Change: Rewiring a 175-Year-Old Company for the AI Era

    What does successful leadership look like in the age of AI, constant disruption, and accelerating change? In this episode, Dan Roberts sits down with Sears Merritt, CIO at MassMutual. Rather than chasing headlines, Sears has spent more than a decade building systems, teams, and cultures that consistently deliver impact, all while staying deeply grounded in purpose, accountability, and policyholder-first service. We are unpacking Sears’ leadership playbook to learn how MassMutual approaches innovation inside a 175-year-old institution, why adaptability is becoming a timeless leadership skill, and how organizations can create environments where breakthrough thinking naturally emerges. Connect with Sears: https://www.linkedin.com/in/searsmerritt/ MassMutual: https://www.massmutual.com/ Listen to learn valuable leadership insights, including: Why impact matters more than recognition or promotionHow to create long-term trust and consistency with customersThe most important leadership skills in the age of AIHow to adapt your “learning rate” in periods of rapid changeHow focusing on outcomes instead of solutions can unlock innovationThe value of a strong CEO-CIO partnership Featuring submitted questions from: Sharmila Ramar, CTO & Global Head of Enterprise Infrastructure Services, MassMutualManoj Vallam, Head of HR Consulting, Enterprise Technology, & Experience, MassMutualSara Biller, Co-Founder, FinTech Sandbox, Board MemberAzer Bestavros, Associate Provost for Computing & Data Sciences, Boston UniversityJosh Alwitt, Leadership & Organization Coach, Josh Alwitt Leadership

    52 min
  2. Coherence in the Chaos: How Leigh Ann Russell is Rewiring Leadership in the Age of AI

    Apr 29

    Coherence in the Chaos: How Leigh Ann Russell is Rewiring Leadership in the Age of AI

    Today’s guest is a technology executive who has mastered the art of honoring a strong legacy while reinventing it in an era of massive disruption. Leigh-Ann Russell is the CIO and Global Head of Engineering at BNY, which was founded 240 years ago. In this episode, Leigh-Ann is opening up her leadership playbook and sharing her perspectives on how to lead through chaos with clarity, why coherence is her defining word for today’s AI era, and how organizations can balance trust, innovation, and transformation at scale. Connect with Leigh-AnnBNY Tune in for expert advice from Leigh-Ann, including: What it takes to safeguard trillions of dollars in assetsHow to build executive alignment around AIOvercoming AI fearsCoherence as a leadership strategyThe power of servant leadershipEmbracing a beginner’s mindset Featuring submitted questions from: Shannon Hobbs, Chief People Officer, BNYAdriana Marquez, VP Upstream Performance, BPKeith Ferrazzi, NYT Best Selling Author, Founder of Ferrazzi Greenlight, Episode 86 GuestNastassja Hagan, Senior Director, COO, Engineering, BNYRowan Eleanor Donachie, University Student, Overachiever

    57 min
  3. The Intangibles of Leadership – Turning the Invisible into Impact

    Apr 8

    The Intangibles of Leadership – Turning the Invisible into Impact

    This episode we’re sitting down with Sanjay Shringarpure, CIO at The Freeman Company, to unpack the intangibles of leadership. These are the qualities you can’t easily measure on a dashboard but are often the key difference between leaders who talk about transformation and those who actually achieve it. Over his two decades of technology leadership experience, Sanjay has built a strong track record of leading major digital transformation projects by drawing on his ability to foster collaboration while delivering innovative solutions. From decision velocity to creating a culture of extreme transparency, he has mastered the intangibles of leadership, and in this episode, he’s sharing how you can leverage them to become a true force multiplier for your company. Connect with Sanjay: https://www.linkedin.com/in/sanjay-shringarpure/ The Freeman Company: https://www.freeman.com/ Tune in for expert insights from Sanjay’s playbook, including: How to leverage speed and preparation to make an impact in the first 45 daysThe concept of healthy impatience and how to channel urgency without creating chaosBuilding a “roundtable” leadership team for healthy debate and growthTrust-building through integrity, sacrifice, and stacking micro wins earlyBalancing candor and compassion Knowing when to push, pause, or pivot through clarity of vision and transparencyDeveloping courage and conviction when the answers aren’t obviousBuilding a culture where leaders grow leadersInstilling the “playing hurt” mindset to show up and lead through tough moments Featuring submitted questions from: Dan Jennings, SVP of IT, The Freeman CompanyEmily Xu, CDIO, EVP, RNDCTarak Patel, CIO, SaiaPaul Fletcher, COO of AV & Event Technology, The Freeman CompanyJohn Dickson, CISO, Insight GlobalRenee Pearson, CIO, Rollins

    1 hr
  4. Denise Russell Fleming: Leading with Trust at Enterprise Scale

    Mar 18

    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 areas Featuring 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

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

    Feb 25

    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

  6. 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
  7. 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
  8. 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
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Trailer

5
out of 5
50 Ratings

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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