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Mike Chessa
It's all about the customer
Professional Background
Mike Chessa is an accomplished professional with a remarkable track record in sales, business development, and executive leadership. With a specialization in driving growth and implementing strategic initiatives across various sectors, Mike has accumulated valuable experience through his roles in several startups and established companies. Over his career, Mike has successfully led two significant acquisitions and has been an integral part of three startups and two scale-up companies. His extensive background allows him to bring a unique perspective and innovative approach to today's rapidly evolving business landscape.
Mike has served in leadership roles such as Chief Revenue Officer at PayShepherd, where he was pivotal in steering the company towards expansive revenue growth while ensuring customer satisfaction. His previous tenure as Senior Global Director at OneTrust for their Governance, Risk, and Compliance (GRC) Specialty department, showcases his expertise in navigating the complexities of compliance in today’s digital age. Furthermore, his influential role as Vice President of Sales at Tugboat Logic—where he guided the company through its acquisition by OneTrust—exemplifies his business acumen and market insight, allowing for seamless integrations and transition of business models.
Over the years, Mike has also held various significant positions as Director at Tugboat Logic, Business Manager at Aconex (which was acquired by Oracle), and Sales Manager at 4castplus. These experiences have not only honed his leadership skills but also built a strong foundation in sales management and strategic planning.
Education and Achievements
Mike Chessa has a robust educational background that complements his professional experience. He studied Bachelor of Arts (B.A.) in Psychology and Philosophy at the prestigious University of Alberta, which has equipped him with a strong understanding of human behavior and critical thinking—skills that are invaluable in sales and management.
Additionally, he has pursued professional certifications that enhance his expertise: a Certificate in Change Management from Prosci, demonstrating his proficiency in leading organizations through transition; Project Management Professional (PMP) certification from the Project Management Institute (PMI), which underscores his capability to manage complex projects effectively; and a Green Belt in Lean Six Sigma from Lean Six Sigma Canada, showcasing his commitment to optimizing processes and improving efficiencies within organizations.
Personal Life and Interests
Beyond his professional endeavors, Mike is a devoted family man with two kids and three dogs, reflecting his grounded and family-oriented nature. He enjoys cooking and savoring good food, which is not just a hobby but a passion that enhances his creativity and brings joy to his family gatherings. Additionally, he is an enthusiastic squash player—a sport that illustrates his competitive spirit and dedication to achieving personal and professional excellence.
Achievements
Through his journey, Mike has achieved significant milestones, including successfully navigating and leading teams through multifaceted transitions during acquisitions, developing high-performing sales teams, and playing a crucial role in the scaling of nascent startups into successful enterprises. His blend of extensive industry knowledge, innovative thinking, and people management skills has resulted in numerous successful business outcomes, setting him apart as a leader in his field.
Tags
Sales Leadership
Business Development
Revenue Growth
Compliance
Project Management
Change Management
Lean Six Sigma
Acquisitions
Startups
Family Man
Squash Lover
