Tech Whisperers: Inside the Playbooks of the Best Digital Leaders

Even among the best technology leaders, there are those who stand out. These are the “CIO Legends” who have not just led their organizations successfully but who have also made an impact that extends well beyond their individual career milestones and across the entire industry. We have featured some of these CIO Legends, including Charlie Feld, Larry Quinlan, Karenann Terrell, and Diana McKenzie, in previous episodes. Today, we are shining the light on Anil Cheriyan, another CIO Legend who has made a mark across multiple industries. Throughout his expansive career journey, Anil has only failed at one thing that we can think of — retirement. After his first retirement, he was called on to serve the federal government. After his second retirement, he took on a different role at Cognizant. Now, in his third retirement, he is driving strategy as a board member, advisor, and investor.In this episode, we are diving into some of Anil’s most important moments and a few of the character traits that have made him the CIO Legend we know today.Tune in to discover:How career experience as both a buyer and a seller in the services industry has influenced Anil’s leadership styleAnil’s leadership strategy that encourages people to step outside of their comfort zonesHow difficult moments have shaped Anil as a leaderHow to approach creating alignment with executive sponsors and maintaining that alignment with the teams that need to deliverHow masterful collaboration has enabled Anil’s career journeyThe role empathy has played in Anil’s personal and professional livesAnil’s strategy for building and investing in a strong network of leadership peersFeaturing submitted questions from:Monty Hamilton, CEO at SparqKathy Kay, EVP & Chief Information Officer at Principal Financial GroupDan Massey, Chief Enterprise Operations & Technology Officer at Region BankAmy Brady, Chief Information Officer at KeyBankElise Bockman, VP of Data at Sherwin-WilliamsScott Case, a three-time CIO

The best leaders are highly intentional about keeping themselves and their teams focused on what matters to deliver high-impact results. Collins Aerospace CIO Mona Bates, who was recently named to the Business Transformation 150™ (BT150), Constellation Research’s elite list of top global transformation executives, is an example of this kind of intentional leader. Her leadership style embraces a multi-faceted approach that is reflected in how she shows up as a business leader first and technology leader second.In this episode, we’re exploring how that approach goes beyond the traditional “I” in CIO, with a focus on seven critical roles embodied by Mona’s leadership: Chief Instigation Officer, Chief Influence Officer, Chief Integrity Officer, Chief Innovation Officer, Chief Insights Officer, Chief Impact Officer, and Chief Inspiration Officer.Tune in to discover:How each of the 7 I’s impact leadership effectiveness and impact How Mona has introduced and executed new digital transformationHow to lead in complex organizations with a diversified customer baseA behind-the-curtain look at Collins Aerospace’s digital transformation journeyHow Mona leverages data and analytics as part of her overall strategyFeaturing submitted questions from:Rebecca Rhoads, Retired President, Global Business Services at RaytheonMike Britton, Retired Executive

The most effective digital leaders today have a clear vision and a laser-like focus that allows them to focus on delivering what really matters. They’re also able to connect the dots for their organization in a way that elevates their team members and accomplishes their goals. It requires both the willingness to look where others aren’t looking and the empathy to understand how new initiatives will impact everyone involved.Brian Abrahamson is a great example of one of these top digital leaders. As the Chief Digital Officer and Associate Laboratory Director for Pacific Northwest National Laboratory (PNNL), Brian is responsible for leading PNNL’s digital transformation strategy and technology innovation to maintain its position as a globally recognized research institution.Tune in to discover:How Brian manages communication for internal stakeholders and end users alikeBrian’s method for shaping the narrative around computing at PNNLHow Brian balances his purpose and goals (the “why” and the “what”) with execution (the “how”)The value of simplification and how to achieve itHow PNNL is approaching the disruption caused by AINew technologies PNNL is implementing to accelerate its workFeaturing submitted questions from:Jerry Cochran, Division Director for Cybersecurity and Digital Operations at PNNLMary-Lynne Giordano, Executive Assistant at PNNLBrian Vladimiroff, Enterprise Solutions Architect at PNNLKirby Amacker, Change Management Architect at PNNL

It’s not every day you get to record an episode with a superstar guest at a superstar location, so when we had the opportunity to interview a legendary CIO on location at the historic Fenway Park, we couldn’t resist!In this episode, recorded inside NESN’s onsite studio at Fenway, we are shining the light on the career journey, leadership philosophies and super powers of Boston Red Sox & Fenway Sports Management SVP & CTO Brian Shield. With his success at renowned companies like FTD, the Weather Channel, and now, the Boston Red Sox, Brian has earned his reputation as an industry innovator whose wide breadth of experience has helped him lead each organization through digital transformation with confidence.Tune in to learn:How Brian has found success solving business challenges through building and maintaining a trusted networkHow leading with empathy has enabled Brian to lead his teams to breakthrough outcomesWhy newer leaders should answer the call when given “stretch opportunities”The biggest benefits Brian has received from working in a variety of industriesHow Brian crafts a winning data strategyHow to cut through the hype of AI to determine its real, tangible business value for your organizationFeaturing submitted questions from:Jamie Head, Chief Digital & Technology Leader, Founder at JRH AdvisoryBill Phelan, Chief Product Officer at BrillionRobert Strickland, Chief Executive Officer & Founder at M37 VenturesKathy Kountze, Global Chief Information Officer at Bose CorporationAnne Margulies, Former Vice President & University Chief Information Officer at Harvard University

Bhavani Amirthalingam’s career spans more than 25 years of experience in key technology and executive leadership roles across a multitude of industries and geographies. She currently serves as EVP, Chief Customer and Technology Officer at a Fortune 500 company. She initially joined the company as Chief Digital and Information Officer before also taking on customer experience and operations after five years in that role. Along the way, she has also answered the call to join a public board.What are the differentiators that have made Bhavani so successful in her role as a CDIO and also set her up to take on broader business accountabilities? On the latest episode of the Tech Whisperers, Bhavani is sharing her journey and highlighting the leadership philosophies and differentiators that have been instrumental to her success, with insights you can apply to your own career journey.Tune in to learn:Why CIOs can also make great Chief Customer OfficersHow to leverage both the CIO and CCO roles to enable and enhance the customer experienceBhavani’s approach to energizing and inspiring her teamThe value of board experience in improving operational skills as an executive leaderA situational leadership approach to influencing decisionsHow to ensure the right leaders are in the right place at the right timeWhy leaders must build the “DNA of change” in themselves and their teamsFeaturing submitted questions from:Linda Jojo, EVP & Chief Customer Officer at United AirlinesJennifer Wischnowsky, Senior Director of Data, Analytics, & Transformation at AmerenLisa Nichols, Chief Executive Officer at Technology PartnersBonnie Timms Hagemann, Chief Executive Officer at EDA, Inc.

Ally Financial is the nation’s largest all-digital bank, serving 11 million customers with a full suite of online banking services, investment advisory, and securities brokerage. In this episode, we are going to give you an inside look at why Ally has been able to achieve so much success.Host Dan Roberts sat down with Ally’s Chief Information, Data, & Digital Officer (CIDDO) Sathish Muthukrishnan and Ally’s Chief Information Security Officer (CISO) Donna Hart to discuss their successful partnership and unpack their individual and collective leadership superpowers.Tune in to learn:The benefits of a strong CIO/CISO partnershipHow Ally earned the CSO50 award and gained executive supportBalancing a direct communication style with open approachabilityThe current state of Ally’s AI and data journeyHow to be in the right place at the right timeFeaturing submitted questions from:Dan Lemont, Divisional CIO for Tech Strategy & Enterprise Tech at Ally FinancialNeal Sample, Chief Information Officer at Walgreens Boots AllianceRaj Kalahasthi, Chief Digital & Information Officer at Baldwin Risk PartnersLawrence Belton, Director, Cyber Security Engineering at Ally Financial

This week is a special one for Tech Whisperers, because not only do we have an incredible guest, but an incredible guest host, as well!In this episode, a longtime friend and colleague, Brian Watson, talks with Xerox CEO Steve Bandrowczak. One of the nine powerhouse leaders featured in Confessions of a Successful CIO, Steve is known as being a fixer–someone who will answer the call when their company needs it most and who knows what it’s like to start from humble beginnings to build something great.Brian will shine the light on Steve’s origin story, how he arrived at Xerox, and so much more.You will learn:How to “prepare” for the CEO roleSteve’s philosophy on running toward greatnessThe reality of loneliness as you rise in leadership rolesHow to tailor communication to different business leaders' languages and attention spansWhy it’s important to preserve a company’s legacyFeaturing a submitted question from:Vicki Hildebrand, CIO & SVP at Blue Cross Blue Shield of Massachusetts

No matter where you are in your career journey, there is always a need to plan for “The Great Pivot,” that moment when you hang up your day job and move into retirement. But many leaders struggle to adequately prepare for the transition as they approach retirement because they’re so heads-down balancing their work, family, and other responsibilities life throws at them.We’ve invited two incredible leaders, Diana McKenzie, a former CIO for Amgen and Workday, and Karenann Terrell, a former CIO at Wal-Mart and CD&TO at GSK, to share their own experiences and lessons learned when it comes to making a successful transition into the next phase of your professional journey. They sat down with Dan Roberts to discuss how they prepared for the pivot, how they’re spending their time in “Chapter 2,” and what you can do to make the most of your time now to plan for a great pivot of your own.Tune in to learn about:When it’s time to start considering how and when you will retireWhat retiring successfully looks likePreparing for retirement while still working full timeLeaning on your digital leadership expertise to help boards make informed digital decisionsFeaturing submitted questions from:Sal CompaniehKirk BallChris NardecchiaSue-Jean Lin

Join the conversation with best-selling author John Rossman as he discusses making big bets, driving change, and the leader's role in high-stakes moments. Learn about his experience at Amazon, how to de-risk initiatives, and access free resources for evaluating big bets.

While many leaders fill their roles with expertise, wisdom, and excellent capabilities, there are some who stand out even among the most successful. These leaders are redefining how their role operates within their organization, creating a truly unforgettable experience for themselves, their team members, and their customers.Gray Nester, the Chief Information Officer at Brown & Brown Insurance, is the kind of leader whose title only scratches the surface of the impact he has on his organization. In this episode, Dan Roberts sits down with Gray at Brown & Brown’s office in Daytona Beach, Florida, to unpack Gray’s tech leadership playbook.Tune in to learn how to:Align your technology strategy with business goalsCreate a culture of ownership in your organizationNurture a collaborative relationship between technology and business executivesTransform your team and your organization by emphasizing talent developmentCare for your team’s emotional wellbeing while always striving to improve, grow, and changeFeaturing submitted questions from:Julie TurpinJ. Powell BrownJeff DryeWill Shupe