Veteran GovTech go-to-market leader joins as the company invests in unified leadership to meet a rapidly expanding market opportunity

TrueRoll, the AI-powered workflow platform built for county assessor offices, has named Brennan Middleton as its Chief Revenue Officer. Middleton, who joined June 1, brings more than a decade of go-to-market leadership in state and local government technology, most recently as VP of Growth at Neumo (formerly Avenu Insights), where he led GTM strategy for a platform serving more than 4,500 government customers across all 50 states. He will oversee sales, marketing, and revenue operations as TrueRoll scales its platform and expands into new workflows and states.

"Our purpose is to make the work of the assessment community easier. We've built the natural partner to the CAMA system of record — a system of action that pre-processes the work — gathering data, connecting it across systems, running eligibility analysis — so staff can spend their time and expertise on the decisions that need them. That's an opportunity in nearly every assessment office in the country, and bringing on a revenue leader of Brennan's caliber is how we make sure the value reaches every one of them," said TrueRoll CEO Tyler Masterson.

Brennan's cross-functional experience is a deliberate fit. The hire comes as TrueRoll has expanded well beyond its origins as a homestead administration tool into a multi-workflow platform covering deeds, protests, business personal property, and citizen intake — opening a substantially larger market and prompting meaningful GTM investment, including this hire.

"County assessment offices touch every property and household in their community — and they deserve technology worthy of the public's trust. I am driven by a simple mission: to help the governments we serve modernize and operate more efficiently, and to make the experience of government easier and more fiscally responsible. TrueRoll has built exactly the kind of system that delivers on that, and I am thrilled to bring it to more offices and build the team that gets us there," said Brennan Middleton.

With Middleton in place, TrueRoll expects to accelerate its expansion into new workflows, new states, and a larger go-to-market organization — all in service of making the work of the assessment community easier.

About TrueRoll

TrueRoll builds AI-powered automation for county assessor offices. Its platform turns the documents and workflows that govern property assessment — exemptions, deeds, protests, transfers, business personal property, and citizen intake — into a connected system of action, helping jurisdictions work faster, more accurately, and with less manual effort. Learn more at www.trueroll.io.

View source version on businesswire.com: https://www.businesswire.com/news/home/20260609031353/en/

I am driven by a simple mission: to help the governments we serve modernize and operate more efficiently, and to make the experience of government easier and more fiscally responsible.