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About TrueRoll™

A revolutionary approach to homestead exemption audits

Build enough data-driven solutions and you begin to get a sense for processes that can benefit from modernized technology.


That was the case for TrueRoll’s co-founders in 2018. 


With more than a decade of experience working in government, Tyler Masterson and Joseph Walsh, PhD, realized that there was an opportunity to improve on the antiquated and often time-consuming processes that are typically used to identify fraudulent and unqualified homestead claims. 


TrueRoll’s modern, data-driven solution relies on machine learning and automation, drawing from thousands of data sources to pinpoint unqualified and unfiled exemptions. This leads to a process that’s more equitable and transparent. 


While data is at the heart of TrueRoll, we pride ourself on delivering holistic, sustainable, and specialized solutions. Formerly known as the Exemption Project, TrueRoll is a veteran- and disabled person-owned business that qualifies for Disadvantaged Business Enterprise in most jurisdictions.

The Team Behind TrueRoll

Tyler Masterson

Chief Executive Officer, Cofounder

Tyler has 15 years of experience as a strategic advisor for public sector leaders with Tyler Technologies, Socrata, and Lagan 311 prior to co-founding TrueRoll. He has a deep understanding of governmental priorities, as well as hands-on experience developing data-centric solutions for the worlds most progressive cities, counties, and states. Tyler holds an engineering degree from the University of Illinois and lives in Chicago.

Joe Walsh, PhD

Chief Data Scientist, Cofounder

Joe has created marketing models for GE, developed algorithms to predict political contests, and served as lead data scientist with the University of Chicago’s Data Science for Social Good program. There, he oversaw 20+ projects taking advantage of data science, such as systems that identify lead poisoning in Chicago households before children get sick and those that reduce harassment of New York City rental housing tenants. Joe got his PhD in international relations, American politics, and econometrics from the University of Alabama; he now lives in Chicago.

The TrueRoll Team

The TrueRoll team includes a group of like-minded engineers and business-savvy talents that rally around public sector initiatives with common goals of social equality. 


Our members have masters degrees in public policy, masters in computer science, experience working for government, the highest security clearance with the U.S. Department of Defense, political science majors, trained educators, fraud analysts, a 15 year veteran of homestead exemption research and our community of angel and venture capital investors.

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Rob Ross

Head of Research & Development

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Jessica Dragan

Director of Sales & Marketing

Mike Sarver

VP of Homestead

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Matt Amann

Data Engineer


Ruth Weatherly

Exemptions Investigator


Tracy Rivera

Exemptions Investigator


Stewart Reed

Customer Success Manager


Sandy Steele

Marketing Manager

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Lee Wells
Sales Development

Tom Schenk Jr


Tom Schenk, Jr. is a researcher and author on applying technology, data, and analytics to make better decisions. He’s currently the director of analytics at KPMG where he leads the smart city and government analytics practice. He’s authored several publications, including a book on data visualization, chapters on education research, and academic articles on a variety of subjects. Tom previously served as Chief Data Officer for the City of Chicago, led education research for the State of Iowa, and has held a variety of positions within academia. Tom is the co-founder of the Civic Analytics Network at Harvard University’s Ash Center for Democratic Governance and Innovation. He is also the current co-organizer of the Chicago Data Visualization Group.


Our goal is to serve your government and its citizens with more accurate information. Unlike other solutions that promote disruptive audits every five years, TrueRoll offers a proactive approach to exemption monitoring that was specifically designed to make it easier for auditors and appraisers to do their jobs and to further a more transparent, equitable government.

The TrueRoll Difference
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