When you’ve spent your career assigning financial strength ratings to insurance companies, you learn a thing or two about what holds companies back, and what pushes them forward.

Matt Mosher is a Strategic Advisor to Stonybrook Capital and the former CEO of AM Best Rating Services. He brings a rare, honest perspective on innovation and the importance of leadership and culture.

Matt doesn’t just talk about what’s possible, he names the patterns. He breaks down four types of organizations and how they approach change:

* Innovation-Driven – Early adopters that experiment, aren’t afraid to fail and shape the future.

* Reactive but Willing – Fast followers that move once others prove it’s safe.

* Cautious – Firms that struggle to modernize and lack internal clarity on how to adapt. Often constrained by siloed teams and legacy systems.

* Coasting on Historical Success – Firms stuck in a comfort zone that don’t feel the urgency to change. Makes them vulnerable to major tech transformations.

He’s clear on what separates those who adapt from those who don’t. We talk about:

* Why innovation stalls and what to do about it.

* How to build organizational confidence around AI and data.

* What responsible leadership looks like under regulatory pressure.

The level of detail companies provide for their financial strength ratings is vast. Few people get a bird’s eye view with the depth that Matt has experienced.

This episode will help anyone leading AI or data transformation where the stakes are high, and the barriers are real.

DON’T DO THIS.

“I was shocked. I didn’t get a single journalist to tell me that this is a career worth pursuing.”

After years spent getting an undergraduate and graduate degree in English, with her sites set on being a journalist, Chloe Frantzis was told by everyone in the field that journalism is a dead-end career. Putting aside what that means for the current state and future of journalism, it was demoralizing to find out that her career aspirations weren’t going to work out as planned.

“The first time my best friend ever saw me cry was because of AI.”

In this Lead The Machine episode, Chloe shares what it felt like to have her dream career disrupted as she realized how quickly AI was reshaping the creative world she hoped to join.

The story doesn’t end there. Rather than cower away, Chloe embraced learning AI and used this new knowledge to rebuild her career path. Today, she works at BoxMedia.IO in London, helping make AI-generated content sound human again.

Are we shortchanging what Gen Z brings to the table?

Chloe shares a message every leader should hear about Gen Z and the future of work.

“People think we’re lazy or glued to our phones,” she told me. “But I’ve seen older adults’ way more glued to theirs. We actually crave work, structure, and collaboration. We grew up with volatility — the iPhone, social media, AI — so we’re not afraid of change. We expect it.”

Chloe believes her generation is built for what’s next. Having witnessed constant disruption, Gen Z doesn’t fear transformation. Rather, they anticipate it, adapt to it, and want to shape it.

We talk about rejection, reinvention, and how Gen Z is redefining creativity and resilience in the AI era.

Chloe’s story is a reminder that adaptability isn’t just a skill, it’s survival.

“We had to invent the math before we could build the model.”

That’s how my dad, Clay Marr, describes his early years at the dawn of Silicon Valley, from his time at Lockheed getting the first man on the moon and at Fairchild launching the semiconductor revolution.

Bottom line: AI requires the research discipline that made Silicon Valley what it is.

Would you believe that AI innovation is directly tied to winning World War II?

The technologies that shaped victory: early computing, radar, and the birth of systems thinking also laid the groundwork for Silicon Valley’s rise. It was bold, long-term, and funded by vision, not quarterly targets.

In this Lead The Machine episode, Clay describes how he carried that spirit forward when product research meant creating what didn’t yet exist.

We talk about what that spirit of invention can teach us today as AI goes through its own identity crisis, still a platform trying to figure out its product strategy.

From the era of semiconductors to the rise of AI, Clay’s perspective is a masterclass in how real innovation happens: through patience, accountability, and a willingness to experiment before the path is clear.

Plus, my dad’s story is straight up cool.

I’ve known Manny Rodriguez for years, and have always admired how he leads: with purpose, vision, and the courage to push the envelope with a sense of urgency to stay on the leading edge.

Few things are more personal than healthcare, except maybe our own careers.Both are being transformed by AI.

So when we sat down to talk about AI’s impact on healthcare, the conversation quickly became about something much bigger: how we adapt, lead, and stay human when technology starts reshaping everything around us.

In this Lead The Machine episode, Manny shares what that transformation looks like inside UCHealth, a $9 billion health system with 35,000 employees and 200 clinical locations. As UCHealth’s Chief Marketing, Experience and Customer Officer, he’s entrusted to create an environment and a brand that lives up to the care patients deserve and a workplace where employees are empowered to deliver.

He rightly points to the leadership challenge of our time: to frame AI more broadly than a tool, and as a test of culture, trust, and empathy.

We explore how to:🤝 Use AI as a partner, not a proxy🧭 Redefine your role before someone else does🔄 Make adaptability your new career metric🗣️ Protect and humanize your brand voice🌱 Treat AI adoption as cultural transformation, not tech deployment

As you listen, consider: What does it mean to lead with empathy and a clear message of adaptability in an AI-powered world?

No question about it, Valen Analytics was well ahead of its time for the property & casualty insurance industry.

Dax Craig co-founded Valen in 2004 and served as it’s CEO until 2017. I came on as the CMO in 2012 and took over as President in 2018, when Valen was a wholly-owned subsidiary of Insurity, a core software provider.

We understood the power of data and the need to collect a lot of it in order to build models that delivered quantifiable results. We built a data consortium where our client’s contributed granular data that was regularly updated to show results over time (from policy, claims, billing and submission records).

That allowed our models to more accurately predict the future profitability and level of risk for individual policies and the overall portfolio. We published an ROI study each year that showed our client’s achieved 2x the profitability and 3x the growth compared to the industry average in workers’ compensation insurance. Powerful stuff.

Getting to that point took some time. From pilot purgatory to change management and adoption issues, we learned how to alter our approach in the early days of predictive analytics. There are many parallels and hard-earned lessons to share for where we find ourselves with AI.

Enjoy this podcast episode and post your comments. Feel free to share the episode with your colleagues.

Kirstin

Hi, I'm Kirstin Marr and so glad you are here! Take a listen for what to expect in upcoming episodes and learn a bit more about my background. Please share this with your colleagues.