Scott Fleszar is an accomplished CEO with over 25 years of experience leading high-growth B2B SaaS companies. Known for his ability to scale businesses, execute strategic M&A initiatives, and lead successful exits, Scott is deeply passionate about developing people and building companies. Throughout his career, Scott has consistently demonstrated a talent for fostering high-performance cultures, inspiring teams, and attracting top-tier leadership. He is recognized for his operational acumen, strategic planning, and ability to drive profitability, operational effectiveness, and sustainable growth.
Most recently Scott was CEO of SafeSend, an Ann Arbor based high growth vertical B2B SaaS business. Under Scott’s leadership from 2019 – 2024, the employee base grew 40 to 180, revenues grew 8X, company culture exceled marked by high employee engagement scores and low turnover, and the business delivered consistent “Rule of 40” financial performance. In 2021, Scott led the successful investment by PE firm Lead Edge Capital in SafeSend at a 10x revenue enterprise valuation. Prior to his role as CEO, Scott served as Chief Operating and Strategy Officer, where he played a key role in building the company’s organizational structure, aligning teams around strategic goals, and driving operational excellence.
Before SafeSend, Scott spent over 20 years at Thomson Reuters Tax & Accounting, where he held various leadership roles, including VP Developing Businesses (P&L responsibility), VP Product Management, and VP Marketing. His expertise spans end-to-end business acumen, mergers and acquisitions, and partnering with investors/stakeholders to align on strategy and maximize enterprise value. Scott holds an MBA from the Ross School of Business at the University of Michigan and a BBA in Accounting from Eastern Michigan University.
Scott’s leadership has earned him numerous accolades, including recognition on the 2023 Inc. 5000 Fastest Growing Companies list and Eastern Michigan University’s Alumnus of the Year award. He is highly regarded for his ability to build durable revenue engines, create innovative go-to-market strategies, and drive high growth results.
Outside of his professional life, Scott is a dedicated family man, proud husband, and father of three, with one child in the workforce and two currently in college.
Character: Scott Fleszar is known for his integrity, inspiring leadership, and commitment to building high-performing, inclusive company cultures.
Knowledge: With over 25 years of expertise in scaling B2B SaaS companies, Scott is highly proficient in strategic growth, M&A, and operational excellence.
Strategic: Scott excels at aligning business goals with long-term strategies, driving sustainable growth, and ensuring transparency in achieving results.
Communication: A highly effective communicator, Scott fosters collaboration across teams, ensuring alignment on vision and objectives while motivating and mentoring top talent.
