Jackson Montgomery is Director of the Data and Insights Division at Think Big, where he drives product strategy and go-to-market execution for the company’s AI-powered tools. He’s helped lead the development of WarRoom—an intelligence platform built for political campaigns and public affairs teams that need to act fast and hit harder with data-backed moves.

Jackson’s focus sits at the intersection of strategy, product, and messaging. Over the last year, he’s been hands-on with large language models—working to translate complex data into usable insight and building tools that actually get used in the field, not just demoed in decks. His edge lies in knowing what teams need right now and building fast, flexible systems that deliver.

Earlier in his career, Jackson built and led high-performing sales teams across both DTC and SaaS—recruiting, training, and managing hundreds of reps and while generating a few million in revenue. He’s known for turning chaos into systems, spotting leverage fast, and leading teams with a mix of clarity, pressure, and real-time problem solving. The teams he leads tend to move fast, punch above their weight, and have fun doing it.

Born and raised in Tallahassee, Florida, Jackson studied Business and Computer tech at TSC and Florida State University, where his family has been Seminole boosters and season ticket holders for over 50 years. He now lives in downtown Tampa with his girlfriend, Ryleigh, and spends most weekends on the golf course chasing scratch.