Chief in Tech Deep Dive Shortcast

What does it take to evolve a company’s culture while scaling from startup to global enterprise?

In this Chief in Tech session, Kate Prouty, Chief Information Officer of Akamai Technologies, shares lessons from her 25-year journey helping transform Akamai from a fast-paced dot-com startup into a multi-billion-dollar cloud and security leader.

Kate reflects on how organizations must mature, how leadership must evolve alongside the business, and why culture is never static. From “obstreperous” startup energy to a flexible, inclusive global workforce, she shares practical insights on driving change without losing what makes a company special.

In this conversation, we explore:

• Why change is not optional—it’s essential for survival
• How leadership must evolve as organizations scale
• Shifting from individual heroics to collaborative team success
• Building cultures rooted in trust, inclusion, and psychological safety
• How to become a catalyst for change—at any level

🎧 Tune in for a candid conversation on embracing growth, challenging the status quo, and leading cultural transformation from the inside out.

What does it truly take to build an inclusive, high-performing workplace in today’s technology landscape?

In this Chief in Tech session, Judy Dinn, Chief Information Officer at TMX Group, shares powerful insights from over 25 years in technology leadership. Drawing from her experience across major financial institutions, Judy explores how diversity, empathy, and balance are not just values, but strategic drivers of innovation and business success.

From navigating non-inclusive environments to building cultures where every voice is heard, Judy offers practical strategies for leaders and emerging professionals alike.

In this conversation, we explore:

• Why inclusion—not just diversity—is the key to unlocking innovation
• How empathy strengthens leadership, relationships, and career growth
• The importance of visibility, sponsorship, and authentic networking
• Practical tactics for fostering inclusive meetings and teams
• Redefining balance at different stages of life and leadership

🎧 Tune in for an empowering conversation on building workplaces where people feel valued, supported, and inspired to contribute at their highest potential.

Gen Z has ushered in a new era of the multigenerational workforce. As organizations navigate shifting perspectives on work, communication, and culture, leaders must find new ways to foster unity across five generations.

In this Chief in Tech session, Anneliese Olson, President, Imaging, Printing and Solutions at HP, and Marah Edelen, Former Director, US Print and Supplies Inside Sales at HP, share real-world leadership insights from decades of experience inside one of the world’s leading technology companies.

Together, they explore how inclusive leadership can bridge generational differences, create stronger collaboration, and empower employees at every stage of their careers.

Key themes include:

• Leadership strategies for managing a five-generation workforce
• Creating cultures of belonging where every voice matters
• Embracing diverse perspectives as a competitive advantage
• Encouraging cross-generational learning and collaboration
• Empowering colleagues to contribute to one another’s success

🎧 Tune in to discover how organizations can cultivate inclusion, learning, and career growth in today’s evolving workplace.

Fear shows up at every stage of leadership, but courage determines how far we go.

In this powerful Chief in Tech session, Lakecia Gunter, Independent Board Director at

IDEX Corporation, shares how leaders can overcome fear, make bold decisions, and lead innovation with confidence in fast-changing tech environments.

Drawing from her journey across multi-billion-dollar businesses, AI-driven transformation, and executive leadership, Lakecia explores what it truly means to fear less and roar more, especially for women navigating high-impact roles in technology.

Key takeaways include:

• The art of making bold, high-stakes decisions
• Building resilience in moments of uncertainty
• Reframing fear as fuel for growth and innovation
• Cultivating courage to lead authentically and decisively

🎧 Tune in for an inspiring conversation on fearless leadership, innovation, and owning your voice at the table.

AI is no longer experimental—it’s operational, strategic, and reshaping how businesses lead and scale. In this session, Linda Yao, VP and General Manager, Hybrid Cloud & AI Solutions at Lenovo Solutions & Services Group, and Poonam Garg, VP at U.S. Bank, share real-world insights on turning AI ambition into business impact.

Key discussion points include:

• Why AI adoption must be practical, people-first, and security-led
• How generative AI is democratizing productivity across industries
• Building AI readiness through strong data, governance, and talent
• Leading change amid rapid technological disruption
• What visionary leadership looks like in an AI-driven future

🎧 A must-listen for leaders navigating AI adoption, scale, and responsibility in today’s fast-moving business landscape.

From moving to the U.S. to leading digital transformation at one of the world’s largest healthcare technology companies, Rashmi Kumar, SVP & CIO of Medtronic, shares her journey to the C-suite and the leadership lessons learned along the way.

In this episode, we explore:

• Taking bold career risks and stepping outside comfort zones
• Driving digital transformation with purpose and business impact
• Building resilient, future-ready leadership skills
• The role of mentorship and sponsorship in career growth
• Leading with vision, adaptability, and inclusion

🎧 Tune in for an inspiring conversation on resilience, transformation, and what it truly takes to lead at the highest levels of tech.

AI is reshaping enterprise strategy, cybersecurity, and the very nature of leadership—often all at once. In this Chief in Tech session, senior technology leaders share candid perspectives on navigating constant change in a rapidly evolving tech landscape.

In this Chief in Tech episode, senior executives Alvina Antar, Chief Digital Officer at F5; Meerah Rajavel, CIO at Palo Alto Networks; Sharon Mandell, Former CIO of Juniper Networks; and Wendy M. Pfeiffer, Founder of Box of Chocolates LLC, share candid insights from the front lines of digital and cybersecurity leadership.

Key themes include:

• How AI is redefining business strategy, productivity, and innovation
• Enterprise approaches to generative AI adoption—from experimentation to impact
• Cybersecurity, risk, and trust in an AI-driven world
• Digital transformation as a continuous journey, not a destination
• The human side of CIO leadership—wellness, resilience, and balance

🎧 Tune in for real-world insights on leading technology when everything is happening everywhere, all at once.

As artificial intelligence reshapes enterprise systems and accelerates threat evolution, technology leaders are navigating a defining moment—where innovation, ethics, and cybersecurity intersect.

In this Chief in Tech session, Aysha Khan (CISO & CIO, Treasure Data), Bhawna Singh (CTO, Customer Identity, Okta), and Stephanie Domas (CISO, Canonical) join a forward-looking discussion moderated by Virginia Mayo (VP, Global Security & Resiliency, Kyndryl).

Together, they explore what it means to lead secure innovation in an era defined by generative AI, identity threats, and systemic complexity.

Key Takeaways

• How AI is redefining the enterprise risk landscape—and the evolving CISO/CTO response
• The growing convergence of cybersecurity, identity, and software architecture
• Executive strategies for AI governance, compliance, and resilience
• Building trust-first cultures that enable innovation with accountability
• Leading through complexity in an AI-driven threat environment

From AI governance and risk strategy to building resilient, trust-first cultures, this executive panel offers real-world insights into cybersecurity leadership at the highest levels.

🎧 Tune in for a powerful conversation on how today’s CISOs and CTOs are shaping the future of secure digital transformation.

From the Bench to the Boardroom: Lessons from Leslie Vander Baan on Resilience, Risk, and Reinvention in Tech

What does it really take to navigate uncertainty, setbacks, and reinvention in a tech career?

In this episode, we hear a candid and deeply personal journey through entrepreneurship, career pivots, and the emotional realities of building, losing, and rebuilding in the tech industry. From blind ambition and launching a bold consumer-to-consumer venture, to scaling nationally with a Fortune 750 partner and facing the devastation of winding it all down, this story offers unfiltered insights into resilience and growth.

We explore key lessons on:

• Turning internal doubt and anxiety into fuel for growth
• Embracing risk and learning by starting before everything is perfect
• Navigating career setbacks, pivots, and unexpected endings
• Making decisions driven by opportunity rather than fear
• The power of reflection, recalibration, and trusting non-linear career paths
• How closed doors can lead to powerful full-circle moments

From entrepreneurial beginnings to leading an AI-powered inspection platform in Silicon Valley, this episode is a reminder that success is rarely linear—and that every experience, high or low, shapes your leadership story.

🎧 Tune in to discover how resilience, adaptability, and self-trust can help you not just survive but thrive, through professional challenges.

Inward to Upward: Lessons from Aysha Khan on Leadership, Clarity, and Redefining Success

What does it take to lead with intention and find fulfillment in both work and life?

In this episode, we explore the transformative leadership philosophy of Aysha Khan, Chief Information Security Officer (CISO) and Chief Information Officer (CIO) at Treasure Data. Drawing on over 20 years of experience at Fortune 500 companies, Aysha has developed a powerful framework for growth, alignment, and impact.

We delve into her insights on:

• The role of exposure and role models in shaping vision and ambition
• Moving beyond work-life balance toward alignment and mission clarity
• Applying the Japanese concept of Ikigai to uncover your purpose
• Building a portfolio of impact across roles—executive, advisor, coach, and more
• Shifting from chasing success to attracting it through energy and intention

Aysha’s journey—from her early days in Karachi to leading in Silicon Valley—offers a compelling blueprint for anyone ready to grow from the inside out.

🎧 Tune in to discover how “Inward to Upward” leadership can help you unlock your full potential.