Brian Pearson

Chief Technology Officer at Bridgeway Benefit Technologies

Louisville, Kentucky, United States

About Brian Pearson

Brian Pearson is Chief Technology Officer at Bridgeway Benefit Technologies. Location: Louisville, Kentucky, United States.

I lead technology strategy and execution as CTO of Bridgeway, where I've spent the last three years doing something a lot of tech leaders talk about but few actually pull off: modernizing decades-old, mission-critical systems without slowing the business down. Bridgeway builds software that powers benefits administration and claims for the Taft-Hartley market — the kind of infrastructure that has to work every single day, for every single customer. A large part of that infrastructure still runs on COBOL and UniData systems built over decades — proven, dependable, and deeply embedded in how our customers operate. Rather than treat that as a liability to rip out overnight, I've led an ongoing modernization effort that starts with understanding: mapping the legacy footprint end-to-end, untangling business rules, resolving entity collisions, and building a deliberate roadmap to bring that functionality onto current architecture — all while keeping the platform running for the customers depending on it today. It's a multi-year journey, not a rip-and-replace, and I'm leading it with the discipline that requires. At the same time, I've driven the org's shift toward practical AI adoption — not AI for its own sake, but AI embedded into how we build, deliver, and support software, from internal tooling to customer-facing capabilities. And I've led new product development efforts that extend Bridgeway's platform into new areas, backed by data-driven rigor: Six Sigma-based analysis of our own delivery data to find and fix the real bottlenecks, not the assumed ones. My approach is the same wherever I apply it: challenge the status quo, back decisions with data, and never let "that's how it's always worked" be a good enough answer. If you're tackling legacy modernization, AI adoption, or building new products in a regulated, high-stakes industry, I'd love to connect.

Skills

  • Service-Level Agreements (SLA)
  • Negotiation
  • Presentations

Additional experience

  • Chief Technology Officer

    Bamboo Health

    April 2022 – August 2023

Education

  • B.CS., University of Louisville - Speed School