In this episode of Portfolio Perspective: Managing Risk & Seizing Opportunity, Andrew Pace sits down with Kareem Jernigan, Executive Vice President and Chief Financial Officer at LAI Fleet, to explore how a 68 year old fleet management company is modernizing its entire technology platform without losing the culture and service model that built its reputation.

For a company built on relationships and a workforce with decades of tenure, replacing a 40 year old legacy system is not just an IT project, it is an identity question. Kareem Jernigan, EVP and CFO at LAI Fleet, has spent the last three years leading exactly that kind of transformation, retiring a homegrown, end to end system that handles everything from prospecting to securitization in favor of a modern platform, without disrupting the culture that has kept employees at the company for 20, 30, even 50 years.

Kareem came to LAI Fleet in July 2020, stepping into an organization with an average employee tenure of 24 years and a leadership team, including a president with nearly four decades on the job, that had built the business on personal relationships and deep institutional knowledge. A CPA with an MBA from the University of Houston and a background in oil and gas before joining LAI Fleet, Kareem also served in the United States Marine Corps, an experience he credits with shaping his approach to discipline and accountability.

Kareem and talk through what it takes to de-risk a technology transition of this scale, how LAI Fleet has approached digitizing paper heavy processes without losing what makes the business unique, and how the company earns credibility with a long tenured, relationship driven workforce during periods of change. They also get into how LAI Fleet competes as a privately held, mid-market focused company against larger, efficiency driven competitors, and how Kareem manages residual risk across a fleet of tens of thousands of vehicles.

The conversation offers a candid look at what it actually takes to modernize decades of institutional process, how financial discipline holds up under real volatility, from COVID to supply chain disruption to rising rates, and what the expanding role of the modern CFO looks like in practice.

Key Topics Discussed:

• Replacing a 40 year old legacy system without losing company identity
• The technical debt that builds up in long running proprietary systems
• What going paperless actually means in vehicle leasing and fleet management
• Earning credibility as an external executive in a relationship driven organization
• Aligning incentives to support a major technology transformation
• Rebuilding the bench while managing retirements and institutional knowledge transfer
• The expanding scope of the modern CFO role
• Financial discipline and credit risk management through market volatility
• Competing as a privately held company in an underserved small and mid-size fleet market
• LAI Fleet’s account executive as fleet manager service model
• Managing residual risk and vehicle liquidity in fleet leasing
• Defining personal and organizational success through succession

Notable Takeaways:

• On modernizing the legacy system:“It’s not going to change who we are. This will allow us to become more of who we are.”
• On process discipline: “Anywhere there’s a lot of friction, it’s not being done well.”
• On discipline as a personal quality: “I think discipline is a personal quality and it’s an inside-out job. It’s something that comes from the individual that you project into and onto an organization.”
• On serving an underserved market: “Less hassle, lower costs, more profit.”
• On financial discipline through volatility: “Slow and steady wins the race.”
• On systems and discipline: “We don’t rise to the level of our goals, we fall to the level of our systems.”
• On defining success: “If my successor can step in and I can hand the baton to them and they can push the ball forward, that’s how I’m defining success.”

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