Mike Chessa
About Mike Chessa
Mike Chessa serves as the Chief Revenue Officer at PayShepherd, bringing extensive experience in sales and leadership from previous roles at Tugboat Logic and OneTrust. He has a background in project management and change management, complemented by a Bachelor of Arts in Psychology and Philosophy from the University of Alberta.
Work at PayShepherd
Mike Chessa serves as the Chief Revenue Officer (CRO) at PayShepherd, a role he has held since 2024. His position involves overseeing revenue generation strategies and driving business growth within the organization. PayShepherd operates in a remote capacity, allowing for flexibility in operations. Chessa's leadership is expected to contribute to the company's objectives in the competitive landscape.
Previous Experience at Tugboat Logic and OneTrust
Chessa previously worked at Tugboat Logic, where he held the position of Director from 2018 to 2020. Following Tugboat Logic's acquisition by OneTrust, he transitioned to OneTrust as the Sr. Global Director - GRC Specialty, serving from 2022 to 2024. Additionally, he was the Vice President of Sales at Tugboat Logic from 2020 to 2022, where he played a key role in sales strategy and execution.
Education and Expertise
Mike Chessa holds a Bachelor of Arts (B.A.) in Psychology and Philosophy from the University of Alberta, where he studied from 2005 to 2009. He has furthered his education with several certifications, including Project Management Professional (PMP) and Lean Six Sigma Green Belt, both achieved in 2015. He also obtained a certificate in Change Management from Prosci in the same year. This educational background supports his expertise in project management and business processes.
Entrepreneurial Involvement and Achievements
Chessa has been involved in two acquisitions and three startups, highlighting his entrepreneurial spirit and experience in navigating complex business environments. His expertise in scaling companies demonstrates a strong capability in business growth and development. This experience positions him as a knowledgeable leader in revenue generation and strategic planning.
Personal Interests and Family Life
Outside of his professional commitments, Mike Chessa has a keen interest in food, which may indicate involvement in culinary activities. He enjoys playing squash, reflecting a passion for sports and physical fitness. Chessa balances his professional life with family, having two children and three dogs, showcasing his commitment to both career and personal life.