Randy Jouben is the Chief of Risk Management in Fairfax County, one of the largest counties in the United States. He shares the lessons he has learned from his varied experiences from non-profit and for-profit to the public sector. He underscores the importance of embracing technology and training employees in AI engagement in order to manage risks instead of being blind to them, shares the benefits of his CPCU designation, and highlights the importance of continued learning at every stage of a successful career.

Key Takeaways:

● Randy's work with Fairfax County from criminal and fire to helping the homeless.

● Randy's literal fall into an insurance career.

● Lessons learned from the non-profit sector.

● Five Guys from the kitchen to the EBITDA bottom line.

● The value of partnering together during the bad years.

● Insights into insurance in municipalities.

● Risk financing in the public sector.

● Legal system abuse and the need to reform.

● Ensuring proper education about utilizing AI.

● Randy's flexible advice to his early career self.

Mentioned in This Episode:

Randy Jouben

Tweetables:

"When you realize how much you can help an organization help their mission, it's more fulfilling than a paycheck."

"If you can partner together in the bad times, it makes the good times so much better for everyone else."

"In municipalities, your neighbor is your boss in one sense or another."

"Just because you've had your job in the industry for 30 years, doesn't mean you stop learning."

"You need to embrace technology and help employees learn it and engage with it so you can manage the risk instead of being blind to the risk. You don't work in risk management and not take risks."

Courtney Davis is the Executive Vice President and Global Education Practice Leader at HUB International. Courtney was a guest on the podcast back in 2022 and has returned for a follow-up interview at the RIMS 2025 Conference in Chicago. She reflects on changes in her career, what it means to effectively educate and engage across a network, and how she is working to be an agent for change and greater diversity at every level in the insurance industry.

Key Takeaways:

● Courtney's journey from the University of Chicago to HUB International.

● The conversations and possibilities that attracted Courtney to her present role.

● HUB's growing footprint in the insurance industry.

● The biggest surprises in Courtney's shift from risk management to brokerage.

● Educating and engaging an entire network.

● Supporting greater diversity at every level in the insurance industry.

● Effective strategies for attracting new talent.

● What it takes to become a change agent.

Mentioned in This Episode:

Courtney C. Davis

HUB International

Tweetables:

"As much as an opportunity may be great, it's who you work with that will make you successful."

"Sometimes you have to be the change agent yourself."

"Don't stop until you see the change that you want."

"Being truly intentional to support the next level of talent is what we have to commit to."

Kyle Thompson is the Senior Vice President in Risk Management at Arthur J. Gallagher, where he leads large teams on complex risk. He played pro golf for 17 years before pivoting to risk management in 2019. In this live from RIMS 2025 episode, Kyle reflects on the ways that his golf career prepared him for risk management. He highlights the similarities between the two careers, reflects on some of his biggest wins, and details the athletic characteristics that have helped him excel in his new career.

Key Takeaways:

● Kyle's experience with golf was a family affair that is in his DNA.

● Advancing through the PGA was a multi-year-long effort.

● Kyle's pivot from pro golf to risk management.

● Risk and insurance knowledge started with earning accreditations.

● Kyle has zero regrets about his career in risk management.

● Reflections on Kyle's biggest wins and AJG's growing success.

● Addressing the male-dominated insurance landscape.

● Surprising discoveries that Kyle made once he joined the traditional workforce.

● Characteristics of ex-athletes who thrive in risk management.

Mentioned in This Episode:

Kyle Thompson

Arthur J. Gallagher

Tweetables:

"I had a few offers to go into real estate, but it just didn't speak to me the way insurance did."

"I was a pro at golf; now I'm an aspiring professional insurance broker."

"I know what I know, and I know what I don't know."

"Golf itself is really nothing but risk management."