Kathy Kay has led technology through some of America's biggest crises. From the Great Recession to California wildfires to a global pandemic, she was the person building systems that kept companies and people afloat.

As EVP and CIO at Principal Financial Group, she brings a battle-tested instinct for building technology through disruption. She has done it at General Motors, PG&E, Comerica, and SunTrust Bank. Every role sharpened her approach to innovating with compliance. That cross-industry depth is exactly what makes her perspective on scaling enterprise AI worth listening to right now.

In this episode of Earn The Right Podcast, she joins Apoorv Agarwal to discuss enterprise AI adoption, the build vs. buy decision for AI agents, and why being a regulated company is no excuse to move slowly.

Kathy shares how she democratised AI across an entire organisation, starting by opening her first ChatGPT study group to attorneys, compliance, risk, and engineers all at the same time. From there, she explains why the one-time cost to build software is always the cheapest part of any program. She also makes the case for why human contact becomes more valuable, not less, as AI automates everything around it.

WHAT YOU'LL LEARN

• Build vs. buy for AI: why the one-time cost is always the cheapest part of any program
• Why outcome-based pricing aligns AI vendor contracts better than seat-based models
• The difference between a mentor and an advocate, and why your career needs both

ABOUT KATHY KAY

Kathy Kay is Executive Vice President and Chief Information Officer at Principal Financial Group. She leads global technology strategy, IT operations, security, and innovation across retirement, insurance, and asset management. Under her leadership, Principal went from 800 to 17,000 active AI users in a single year across a workforce of 20,000. She was inducted into the US CIO Hall of Fame in 2026. She won CIO of the Year at the Technology Association of Iowa's 2023 Prometheus Awards. Before Principal, she served as SVP and CIO at PG&E during the California wildfire crisis, CTO at SunTrust Bank, and SVP and CTO at Comerica through the 2008 financial crisis. She began her career at General Motors Research Labs and OnStar, building connected vehicle systems that saved lives.

ABOUT EARN THE RIGHT PODCAST

How do the world's most impactful leaders think, decide and build? Through unfiltered conversations, the Earn The Right podcast takes listeners inside the rooms where the hardest choices are made: from building billion-dollar companies to navigating doubt, reinvention and change. The show is hosted by Apoorv Agarwal, an AI scientist, entrepreneur (Text IQ, acquired 2021) and Columbia PhD, who has advised Fortune 500 leaders. For founders and decision-makers developing the future, this is your front-row seat to how the best earn the right to lead.

Subscribe to Earn The Right for conversations with the world's most influential leaders.

Thirty years ago, a rejection letter changed internet history.

Randy Milch never planned to be a General Counsel. He wanted to be Secretary of State. When President Reagan fired all 300 diplomats-in-waiting on his first day in office, Randy went to law school instead.

What followed was two decades at the center of American corporate history. As General Counsel of Verizon, Randy navigated the MCI merger, NSA surveillance, and telecom deregulation. When the government's secret surveillance program became front-page news in 2005, he was the lawyer managing it from the inside.

Randy's argument in this episode is uncomfortable: America is protecting the wrong thing. Billions go toward litigating individual data breaches; power grids, water systems, and critical infrastructure remain exposed. He makes the case for a tiered cybersecurity standard that forces a national reckoning with what actually needs protecting.

On AI, he is skeptical but not dismissive. He watched billions pour into dot-com infrastructure in the late 1990s. He was inside one of the companies whose networks ran it all. He knows what a cycle looks like before it turns. The questions he is asking about AI today are the same ones few were asking in 1999.

That experience is exactly what he now brings to NYU, where he co-chairs the Center for Cybersecurity and built one of the first programs training lawyers and engineers to understand each other's risks and blind spots.

In this episode, we cover:

• Why risk aversion is a lawyer's greatest liability

• How Verizon won long distance by losing the right way

• What the NSA surveillance crisis taught Randy about leading under pressure

• Why America is solving the wrong cybersecurity problem

• What the dot-com boom tells us about the AI moment we are in now

• Why engineers and lawyers need to close the gap between legal liability and technical reality

Subscribe to Earn The Right for conversations with the world's most influential leaders.

What does it take to protect the world’s most powerful financial institution for nearly three decades?

In the fifth episode of Earn The Right, Apoorv Agarwal sits down with Greg Palm, the legendary former General Counsel of Goldman Sachs. The story of this small-town bred lawyer is a striking departure from the typical Wall Street pedigree.

Growing up in Chenango Bridge, New York, Greg was the son of parents who never attended college. His path was paved by merit and curiosity, sparked by the national push for science education following the launch of Sputnik.

He attended MIT on a scholarship before completing a joint JD/MBA at Harvard. Before joining Goldman, Greg honed his legal expertise as a clerk for Hon. Judge Henry Friendly and Supreme Court Justice Lewis F. Powell Jr., followed by a prestigious partnership at Sullivan & Cromwell.

Over a 27-year tenure spanning five CEOs, Greg served as Goldman Sachs’ top lawyer, navigating the bank through its 1999 IPO, the 2008 financial crisis, and aggressive regulatory battles. This conversation provides unparalleled insight into high-stakes leadership, the intersection of law and business, and building structural integrity when the global economy is on the brink of collapse.

In this episode, we explore:

• The 2008 Financial Crisis: A behind-the-scenes look at survival strategies, the Abacus settlement, and the emotional weight of leading through a black swan event.

• The Power of Focus over Networking: Why Greg considers himself an outlier who prioritized merit and deep work over intentional networking early in his career.

• From Theory to High Stakes: How a student of theoretical physics and economics at MIT became one of the architects of the modern Goldman Sachs Group.

• Investing in the Unknown: Why a lawyer now bets on the future of space and biology to keep his mind sharp.

• Empowering Autonomy: Greg’s philosophy on building a massive legal department by hiring partners who refuse to be looked over their shoulder.

• The Myth of Gordon Gekko: Why the sleazy Wall Street stereotypes portrayed in movies couldn’t be further from reality.

For more deep dives into the crucial decisions and character-defining moments of world-class leaders, subscribe to Earn The Right.