Meet Our Leadership Team

Tom joined Fleetworthy in 2020 with over two decades of executive experience in the software, technology, and data industries. He specializes in managing and growing technology firms, building great teams and scalable operations. He comes to us after 11 years with RDC (Regulatory DataCorp, Inc.) as President and Chief Operating Officer as the high growth Software/Data-as-a-Service company became a leader in fighting financial crime, helping protect approximately 1,000 banks and financial institutions and 35,000 compliance professionals globally before it became part of Moody’s Analytics. He has undergraduate and MBA degrees from the Wharton Business School, and in his spare time, Tom has a passion for travelling the world with his wife and three kids learning about cultures and history (and food!).

Michael is President and Chief Strategy Officer of Fleetworthy. He has over 25 years of experience managing sales and account management teams delivering SaaS solutions to global organizations. After holding successful management positions at Purchasepro, Perfect Commerce, Capgemini and Sciquest, Michael joined Fleetworthy in 2017 as the Executive Vice President of Sales. In 2019, he was named President and has led company growth through strategic acquisitions, critical partnerships, and positive leadership, making Fleetworthy a leader in the transportation safety and compliance industry.

Jason is joining Fleetworthy as the new Chief Financial Officer (CFO) and will be leading the Finance organization. Jason will oversee all aspects of accounting, finance and FP&A. Jason’s previous role was as CFO of SMS Assist, an Insight portfolio company in the PropTech space. Prior to joining SMS Assist, Jason worked in Public Accounting. He is a licensed CPA in the state of Illinois.  In his free time, Jason enjoys spending time with his wife and two kids.

Cindy joined Fleetworthy in 2021 with more than 10 years of experience building and scaling programs to drive successful outcomes for customers. She most recently served as Senior Director of Growth at RDC, a leader in fighting financial crime. In her role as Chief Customer Officer, Cindy works to ensure Fleetworthy continues to offer a best-in-class customer experience through growth and execute on strategic initiatives that deliver added value for customers, helping drive operational excellence through actionable insights that support saving time and money. Outside of work, you can usually find her busy spending time outdoors with her husband, 3 sons and 2 dogs.

Jason joined Fleetworthy in 2022 with more than 25 years of experience driving results across multiple industries and SaaS companies. He most recently served as the Vice President of Sales and CRO at GPS Insight, where he developed the strategic go-to market plan, product positioning, and revenue growth for the organization. In his role as Chief Revenue Officer, Jason will oversee the sales and marketing teams and support revenue management functions. Jason currently resides in Scottsdale, Arizona with his wife, Loray, and enjoys visiting his children, Drew and Jill at college in California. 

Chao joins Fleetwothy as CMO with deep experience in growing companies through strategy and transformational improvements. Chao recently served as CMO and Chief Growth Officer for Appspace, a leading workplace management software company backed by private equity firm Accel-KKR. Prior to Appspace, he held sales and marketing leadership positions at other private equity backed companies, including DealerSocket, Stack Sports, and Cvent.

Demmons joins Fleetworthy as CPO, with more than 25 years of experience in product and development across multiple industries, including commercial transportation. Most notably, Demmons served as CPO at GPS Insight, a fleet management and field services company, where he was responsible for the strategy and execution of all product and development related activities.

Michael brings approximately 15 years of proven technical business leadership and software development experience to Fleetworthy where he manages the company’s development teams. Previously, he was vice president, technology, at IEEE GlobalSpec, and he also served as director, product development and delivery, for IHS. He earned his computer science degree from Siena College, as well as an Essential Management Skills for Emerging Leaders Certificate from Harvard Extension School.

Dave joined Fleetworthy in 2021 with more than 20 years of Human Resources experience. He most recently served as the Chief People Officer at Auto/Mate Dealership Systems before their acquisition by DealerSocket. Under his leadership, Auto/Mate was awarded “Best Places to Work” and “Top Workplace” in Albany’s Capital Region for 10+ consecutive years. In his role as Chief People Officer, Dave will bring his obsession with culture and engagement to make sure that Fleetworthy employees love coming to work every day. Dave enjoys spending his free time outdoors with his wife and two daughters. He also serves on the Board of Trustees for Make-A-Wish of Northeast New York.

With 15+ years of experience in Client Services, Rachael Doyle is dedicated to delivering exceptional value and fostering employee growth. As a subject matter expert in compliance, she has consistently guided teams to navigate complex regulatory landscapes while ensuring optimal service delivery to not only meet but exceed industry standards. Prior to being promoted to Executive Vice President, Rachael held numerous roles within the company, allowing her to understand all aspects of not only the business, but the industry as a whole.

Ali Knowlton is Vice President, Head of Transformation at Fleetworthy. Since joining the company in 2013, Ali has successfully led the communications, marketing, and customer operations departments. With over 20 years of experience in customer service, project management, and strategic leadership, she now drives transformative initiatives to enhance operational efficiency and business growth. She is dedicated to maintaining transparency and proactive risk management, ensuring that projects align with the company’s strategic objectives.