Welcome to My Professional Story

This site is to help me find a home within an insurance agency. Ive been outside agencies working with Assurex Global and Ennabl for the last 8 years. Im ready to take all that I have learned from the over 160 agencies I have worked with to a new home. A long term one.

I started my career in agencies. I was in two for 15 years and it was the best part of my journey. Working with AM's, Producers and Senior leaders to solve complex problems together. Not data problems, or tech problems but agency problems.

A relevant depiction of philosophy or work ethic

I believe data should do more than inform—it should inspire decisive action and tangible results. In an industry as dynamic as insurance, it’s not enough to simply understand the numbers; you have to understand the behaviors and processes behind them. I focus on how daily agency operations, team decision-making, and organizational habits influence key metrics, ultimately shaping the outcomes we aim to achieve. By blending a deep knowledge of agency workflows with a strategic, data-driven mindset, I strive to move beyond dashboards and spreadsheets toward meaningful, measurable impact.

My approach is grounded in collaboration and curiosity. I engage closely with teams—from account executives and analysts to frontline agents—to uncover the “why” behind the numbers. Through transparent communication, I help turn complex data into actionable insights that empower individuals, streamline operations, and propel growth. Each data point is an opportunity to identify what’s working, refine what’s not, and drive positive change.

I’m looking to partner with a forward-thinking organization that values innovation, embraces new ideas, and nurtures a supportive culture. To me, a progressive environment is one that encourages experimentation, celebrates learning from both successes and setbacks, and fosters a sense of shared purpose. In that setting, I can combine my passion for data interpretation, operational insight, and team-driven initiatives to fuel sustainable progress—and help lay the groundwork for the insurance agency of tomorrow.

History

Lanier Upshaw
(Vice President, Director of IT)
The Crichton Group
(IT Director)
Assurex Global
(VP, Technology and Data Management)
ennabl
(Head of Customer Success)
Your Company
(Future Opportunity)
2002-2012
2013-2018
2018-2021
2021-2024
2025
2002-2012
2013-2018
2018-2021
2021-2024
2025

I was born in Tampa, Florida, and grew up as a military brat, spending most of my childhood on bases in Germany before graduating high school in Ramstein. After that, I enlisted in the military and spent four years with the 101st in Clarksville, Tennessee. A short, not-so-great attempt at college at APSU followed, and then life took a big turn: with a daughter on the way, I discovered a passion for computers. I earned some certifications, and my small family moved from Tennessee back to Tampa so my spouse could pursue her education.

That’s where I landed my first role in the insurance industry—at Lanier Upshaw. Starting as a junior systems administrator, I quickly moved into an executive position and spent the next decade immersing myself in data, insurance finance, and operations. I’m a nerd at heart, and I’ve always learned best by building things, so this was perfect for me. Once my wife graduated from dental school, we headed back to Clarksville, where I joined The Crichton Group (TCG). Drawing on what I’d learned, I helped TCG transform into an award-winning, innovative agency that sold at a high multiple six years later.

Next up was Assurex Global, which took me all over the world—Europe, Australia, across the U.S.—introducing me to top-tier insurance agencies. These firms had great margins, engaged teams, and thriving cultures, and they helped me realize my true passion: working closely with agency teams to nurture positivity, accountability, and genuine support. After three years collaborating with some of the best agencies out there, I joined Ennabl as employee number four. It was back to square one—no product, no clients, no staff—but we built it up together, ending up with about 80 clients and over 60 employees. During that growth, I touched everything from product development to sales, and eventually led our Customer Success department.

On a personal note, I have two daughters, two dogs, and a cat. I share my life with my partner, Tess, and we’re both excited about the next phase of our journey. My daughters keep me inspired every day, fueling my creativity and energy. Above all else, I prioritize my relationship with them, because at the end of the day, that’s what really matters.

Illustration for history

Skills

Insurance Agency Operations

-24 years in the trenches brings alot of understanding.

Communication

-It doesnt matter how smart you are if you make others feel dumb.

Data Analytics

- Everyone has data. Few use it.

Problem Solving

- There is great satisfaction in solving problems large or small.

Leadership

- Provide safety to the team so they can be creative and innovative. Hard conversations should happen quickly.

Technology

- Its not about how much you have but how you use it.

Advantages

- What I consider my super powers.