Matt Leitterman

About Matt Leitterman

If there’s one thing people notice about me right away, it’s the energy I bring into sales and distribution. I love this work because it gives me the chance to connect with people, understand what the market is telling us, and build solutions that meet real‑world needs. I’ve always believed that if you stay curious, stay engaged, and stay close to the customer, the path forward becomes pretty clear.A great example of that philosophy in action is the development of Association Health Plans. It started as a simple idea to give organizations more flexibility, better cost options, and stronger wellness offerings. But the real reason it took off is because we listened. We stayed connected with the associates closest to the market, and together we built something that now supports client groups and more than customers. It’s a perfect illustration of how good ideas become “winning programs” when people are empowered and aligned.While I’m deeply rooted in sales and market strategy, I also bring a natural leadership style that’s focused on encouragement, clarity, and helping people do their best work. I don’t believe leadership has to be loud — it just has to be consistent and people‑centered.Along the way, I’ve had the opportunity to support growth across several areas, including:Driving 18.4% year‑over‑year Medicare Supplement membership growth, surpassing total members.Expanding the Med Supp footprint into 10 new markets, increasing customer acquisition by 20% YoY.Contributing to commercial initiatives that delivered 15% annual membership growth, supporting medical and specialty customers.Across every role and every challenge, one belief has stayed the same:People and the market will always point you in the right direction — if you take the time to listen.That’s the mindset I carry into every opportunity: show up with energy, stay connected to the people doing the real work, create solutions that matter, and lead in a way that lifts others while never losing sight of the customer.

Experience

1. Medicare Supplement Director

   Humana

   Jul 2022 — Present · Louisville, KY, US

   After 17 years in Commercial Group Insurance, I made the jump to the Retail side of Humana—and to say I was intimidated is an understatement. I went from something familiar, predictable, and comfortable to something completely new. But I’ve learned that if you’re not a little uncomfortable, you’re probably not growing. So I leaned into the discomfort, trusted the process, and it turned out to be one of the best decisions I’ve made in my career.That leap landed me on the Medicare Supplement Sales & Distribution team. And wow—what a ride. The business has evolved faster than I ever imagined, and I’ve grown right along with it. The deeper I got into this work, the more personal it became. I developed a clear, firsthand understanding of just how overwhelming it can be for seniors to navigate Medicare. That realization became my North Star. Every strategy, every conversation, every decision is centered around making the experience easier, clearer, and more supportive for the people who rely on us most.What started as a leap into the unknown has turned into a role that connects deeply with both my head and my heart. I’m passionate about growing the business, yes—but even more passionate about helping seniors feel confident, supported, and valued at a time in their lives when they deserve clarity, not confusion.And that’s what keeps me fired up every day.

Education

• Missouri State University

  Bachelor of Applied Science (B.A.Sc.), Business Administration and Management, General

  1994 — 1999

Skills

• Sales
• Team Building
• Health Insurance
• Insurance
• Leadership
• Employee Benefits