Before joining RocketDocs, Jason served as an experienced management consultant, specializing in growing and restructuring middle-market organizations. Jason served as acting CEO and president of Maryland Proton Treatment Center, a Baltimore cancer treatment facility. He has also served in a variety of senior executive positions, including as CEO of EntreQuest, a high-growth sales and leadership consulting, training, and staffing organization he co-founded and sold, and as COO of Florida-based Progressus Therapy.
Jason serves on a number of corporate boards. He holds a bachelor’s degree in economics and political science from Yale University, and a juris doctorate, specializing in finance and taxation, from The University of Maryland.
Bob has served as COO since 2017. He brings over 20 years experience in technology leadership and Customer Success. In addition to his role as COO, he serves as a growth advisory board chairman at FITCI, a Frederick-based startup incubator.
Previously, Bob served in various customer-facing executive roles at emerging- and high-growth SaaS companies. He was a management consultant at ManTech International and he lead the Professional Services business at Spirent Communications.
Bob earned a MS in International Business from Johns Hopkins and a BS in Management from the New School for Social Research after serving as a nuclear operator in the US Navy.
Scott Winn has over 40 years of business and military leadership and management experience, enjoying success in commercial, government, and international sales and business development. A retired Military Intelligence Officer, Scott has held leadership positions in startups, mid-size businesses, and large public companies, including TESSCO, Gartner, RAKKOON, Tresys Technology, EDS, and MCI WorldCom.
Scott is a Trustee at the St. Paul’s Schools, and holds a BS in Political Science from Excelsior College and an MS in Management and Leadership from Western Governors University.
Jeremy has performed as a managing partner of Antson Advisors, a Baltimore-based management consulting firm, specializing in growth initiatives for middle-market companies. He served as interim VP of sales and marketing at Maryland Proton Treatment Center, a free-standing cancer treatment center, where he led the growth of patient volumes by 82% while simultaneously decreasing the overall sales and marketing costs by 35%. Jeremy has served in numerous executive positions for various operating companies. He was managing director of EntreQuest, a high-growth sales and leadership consulting, training and staffing firm where he drove strategy and growth planning.
Jeremy holds a bachelor’s degree in finance from The University of Maryland.
Reanna has served as VP of Customer Success since 2017 and has spent more than a decade working in sales, operations, and customer service. Helping clients achieve their business goals through implementing solutions that boost team performance is at the core of Reanna’s experience.
Before joining Proposal Software, Reanna served as the US VP of Customer Experience for Les Mills, a global fitness technology and content delivery organization headquartered in Auckland, New Zealand. Reanna was on the senior leadership team, during which time she was instrumental in consolidating six US-based distributorships into one large-scale organization. During this time, she started the first Customer Success team, which helped simplify and elevate the way clients interacted with the business.
Reanna holds a BA in International Business and Spanish from Towson University.
Gary has been part of the RocketDocs team since 2018 and is the resident Number Cruncher in his role as Vice President of Finance. His key responsibilities include managing the Company’s financial health, while overseeing finance, accounting, administration and human resources related matters for the company.
Gary began his career working in New York City and Northern Virginia at public accounting firms. He then transitioned to focus on financial transformation in the technology industry, where he has held various leadership positions. Gary holds a BA in Accounting and an MBA.