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.

Puneet joined Fleetworthy in 2025 with over two and a half decades of leadership experience in finance and capital markets, business operations, and corporate strategy, in the software industry. Prior to Fleetworthy, Puneet served as Chief Financial Officer at Pax8, where he helped the company through a period of rapid growth of tripling its revenue, expanding globally, and preparing for an IPO. He also held senior leadership roles at KORE (which he took IPO), Lochbridge (which he took to a strategic exit), and PRGX, bringing expertise in finance, M&A, raising capital, business operations and corporate strategy. Puneet started his career as a management consultant at Booz and Company’s Technology, Media & Telecom practice and at Oliver Wyman. He holds a CFA charter, an MBA, and a Bachelors in Computer Science. Outside of work, Puneet enjoys reading, traveling with his wife, and exploring new technologies including most recently with Machine Learning and Artificial Intelligence.

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.

Dillon joined Fleetworthy in early 2025. Prior to Fleetworthy, Dillon was the Chief Revenue Officer at Via where he built the sales and customer success teams and scaled the business to more than 800 cities in 40 countries. Dillon is a former Term Member at the Council on Foreign Relations and a founding member of the Ambassador Council at the International Crisis Group. He holds a BA in History from Trinity College in Connecticut, an MBA in Finance from the University of North Carolina, and speaks Turkish. Dillon enjoys spending time hiking and exploring the outdoors with his partner and three children.

Scott 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 joins Fleetworthy 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 brings 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 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 is Chief of Staff 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.

Tony joined Fleetworthy in 2023, bringing over 20 years of leadership experience in high-growth software organizations. As Senior Vice President of Revenue Operations, Tony drives alignment across sales, marketing, and customer success to elevate performance and accelerate growth. Known for his pragmatic leadership and operational discipline, Tony is passionate about developing high-performing teams and driving sustainable results. Before joining Fleetworthy, he held senior leadership roles at MetricStream, Kony Inc. (now Temenos) and Oracle, where he led global teams, built scalable revenue models, and executed transformational go-to-market strategies that drove measurable business impact.