Tech Whisperers: Inside the Playbooks of the Best Digital Leaders

This episode of Tech Whisperers is dedicated to the transformational leaders–those who have the courage and vision to make big bets and the endurance and fortitude required to deliver on them. There is perhaps no one better to talk about this than John Rossman, Author of The Amazon Way and Think Like Amazon. His newest book, Big Bet Leadership, has just launched, so we invited John to celebrate his new book and talk about how leaders can acquire the tools they need to make the big bets and follow through on them. 

Tune in to learn about:

• John’s experience working at Amazon and the Gates Foundation
• What it takes to leave a safe path and make risky, impactful moves
• How to create clarity, maintain velocity, and de-risk initiatives
• What every leader needs in high-stakes moments
• The leader’s role in driving change
• How to access free resources for evaluating big bets

Featuring submitted questions from:

• Jim Harding
• Kevin McAffrey
• Stephen Wilson

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 goals
• Create a culture of ownership in your organization
• Nurture a collaborative relationship between technology and business executives
• Transform your team and your organization by emphasizing talent development
• Care for your team’s emotional wellbeing while always striving to improve, grow, and change

Featuring submitted questions from:

• Julie Turpin
• J. Powell Brown
• Jeff Drye
• Will Shupe

As the CIO and Principal over Digital, Data, and Operations at Edward Jones, Frank LaQuinta is laser focused on delivering extraordinary experiences to his team and to clients. With a mandate to future-proof the organization and transform the foundation of the Fortune 500 company, Frank’s leadership, vision, and strategy have to be clear, firm, and tenacious.

In this episode, we stop by the Edward Jones office in person to talk with Frank about his career journey and unpack his tech leadership playbook so you can learn how to: 

• Maintain your competitive advantage
• Develop and implement a digital roadmap for modernizing the enterprise and optimizing technology integration
• Adopt three mindset shifts that will transform your leadership and your team
• Set clear priorities and ensure appropriate funding

Featuring submitted questions from:

• Bobby Anselmo
• Kevin Adams
• Andy Miedler
• Kristin Johnson

Just as the CIO role itself is evolving and transforming alongside technology, so are the processes and the businesses that use them. To be successful in this ever-changing landscapes, leaders need to be adaptable, knowledgeable, and effective visionaries. 

That’s why we are featuring Jim Chilton, EVP & CTO at the Cengage Group. As an experienced business and technology executive, Jim is skilled at driving innovation and optimizing technology by drawing from the lessons he has learned throughout his own career journey. Those skills have helped the Cengage Group maintain their position as a leader and premier disruptor in the edtech industry.

As we unpack Jim’s leadership playbook in this episode, you’ll learn how to:

• Apply insights from the way immersive learning experiences, VR, and AI are being integrated into education
• Transition to new technological paradigms
• Position yourself as a strategic contributor in your organization
• Use “relentless prioritization” to effectively manage time
• Balance accountability and good intentions
• Establish your leadership legacy

Featuring submitted questions from:

• Josh Reibel
• Lorie Page
• Jarrod Mayes
• Bob Solis

One of the biggest realities facing CIOs is the fast-paced evolution of their role and the scope of their responsibilities, especially with new AI tools taking the world by storm throughout 2023. We’ve invited two top executive recruiters to help us navigate the seemingly murky waters of what it takes to be a CIO of a large enterprise today and what organizations are looking for in their recruitment efforts as they move into 2024.

Shawn Banerji is the Managing Partner for the Data, Digital, and Technology Leaders Practice for Caldwell. He is an expert on change management and helps his clients navigate the convergence of talent and technology and its implications across all facets of the evolving digital enterprise.

Martha Heller is the CEO of Heller Search, a premier executive search firm specializing in technology executive search. Throughout her career, Martha has recruited hundreds of CIOs, CTOs, architects, and other senior technology positions. She was the founder of the CIO Executive Council and is the author of two books: The CIO Paradox: Battling the Contradictions of IT Leadership and Be the Business: CIOs in the New Era of IT.

In this episode, we discuss:

• What companies need to do to attract top tech resources
• How CIOs can create thriving, productive cultures for remote and hybrid work
• The need for CIOs to be both digitally and business savvy
• The increasing need for digital literacy across leadership roles
• The biggest challenges facing CIOs
• How to navigate the unprecedented pace of change large enterprises are dealing with today

Ghada Ijam serves as the CIO for the Federal Reserve System, one of the world’s most vital and complex organizations, affecting the economy on an international scale, providing stability to the financial services industry, and facilitating trillions of dollars of payments daily.

In her role, Ghada oversees both the technology and cybersecurity arms of the organization, collaborating with both internal leaders and external vendors to drive great decision-making and innovation while shaping the Fed’s digital future.

Tune in to learn from Ghada’s leadership playbook, including how she:

• Navigates a complex federated structure to lead the Fed’s technology organization
• Motivates and keeps her team excited about supporting the Fed’s mission
• Instills confidence in her team during times of change
• Balances crisis response and long-term strategic planning

Featuring submitted questions from:

Don Anderson

Dan Anthony

Louise Willard

Tammy Hornsby Fink

Dee Waddell

Amir Kazmi is the Chief Information & Digital Officer at WestRock, a $20 billion Fortune 200 company that provides packaging solutions for countless industries. Working as a leader in such a large and established organization means that Amir is responsible for both developing and executing WestRock’s global information systems, technology, and cybersecurity strategy. As if that weren’t enough, Amir is also leading WestRock’s digital transformation with a focus on operations and both customer and commercial digital solutions. 

Tune in to learn from Amir’s career journey, including how to:

• Embrace full ownership for P&L
• Lead digital transformation initiatives in large organizations
• Celebrate efforts and small wins without losing sight of end goals
• Stay adaptable and flexible while pursuing specific business goals

Featuring submitted questions from:

• Shan Cooper
• James Dallas
• Abraham Kazmi

What exactly does it take to lead a 213-year-old company through a digital transformation initiative? How about an enterprise CIO whose career has spanned amazing companies like IBM, KeyCorp, and BMO. Someone who knows how to break out of comfort zones, make tough calls, and stay confident in the face of uncertainty.

In this episode, we are featuring Deepa Soni, Enterprise CIO at The Hartford, a $22 billion property and casualty insurance company. Deepa is responsible for the overall strategy, vision, and execution of business technology, cyber, data analytics, and data science.

Tune in to learn from Deepa’s “answer-the-call” journey and uncover powerful insights from her story, including how to:

• Harness continuous learning to stay adaptable to new technologies
• Actively involve middle management in the change management process
• Engage senior leadership to improve their understanding of AI technology
• Prioritize pace over precision and progress over perfection
• Take a business-centric approach to technology

Featuring submitted questions from:

• Silja Pandaran
• Jamie Patel
• Vipin Gupta

From 8 years in Big Four consulting, to 20 years across three global CPG companies, to now the COO of Latin America’s largest bank, Banco Itaú, Marina Bellini has developed a wide breadth of leadership expertise. 

She has honed her skills to be intentional and laser-focused on the customer while effortlessly balancing fearlessness and courage with kindness, empathy, and gratitude. 

In this episode, we are celebrating Marina’s incredible career journey and unpacking key learnings from her tech leadership playbook, including how to:

• Approach leading a major operating model transformation
• Successfully transition into different industries
• Encourage different perspectives in executive teams
• Maintain a customer-centric approach when driving organizational transformation
• Measure your impact as a digital leader

Featuring submitted questions from:

• Angela Yochem
• Carlos Sanchez Fanjul
• Cenan Orcaner
• Andrea Carpes Blanco
• Marianna Amssoms
• Ricardo Neves

The best leaders don’t only pay attention to how they engage with those on their teams, they also devote their attention to how they show up every day. These leaders recognize that leadership begins before there is even anyone else to lead.

At Generac Power Systems, CIO Tim Dickson is a leader who knows how to consistently show up, which allows him to seize every opportunity that comes his way to transform his team’s, his role, and his entire organization. In this episode, recorded live at the CIO 100 Awards in Southern California, we are unpacking key learnings from Tim’s tech leadership playbook, including how to:

• Lean into your personal strengths to enable your organization’s rise to the next level
• Identify and leverage opportunities to elevate IT’s role in your organization
• Invest in your team members to enrich their experience, skills, and opportunities 
• Be a high-energy leader even during hard days 

Featuring submitted questions from:

Neal Sample

Angela Yochem