Brett Jackson is a seven-time CEO and two-time COO with 35 years of experience scaling and transforming software and software-as-a-service companies with revenues ranging from $5M to $150M, both private and public. He has led companies through scale-ups, pivots, and turnarounds, predominately in the cybersecurity and analytics markets. Prior to his CEO roles, Brett gained extensive functional experience in go-to-market and product, having held multiple VP-level roles in Product Management, Sales, and Marketing.
The operator behind the coach
Brett Jackson is a seven-time CEO and two-time COO with 35 years of experience scaling and transforming software and software-as-a-service companies with revenues ranging from $5M to $150M, both private and public. He has led companies through scale-ups, pivots, and turnarounds, predominately in the cybersecurity and analytics markets. Prior to his CEO roles, Brett gained extensive functional experience in go-to-market and product, having held multiple VP-level roles in Product Management, Sales, and Marketing.
As an experienced operator, Brett firmly believes that time is the real enemy and success requires relentless, focused execution, with a high sense of urgency, by a collaborative, high-performance team. He embraces challenges, finds fulfillment in a company’s journey to higher performance, and appreciates that a CEO’s work is never done.
Brett earned a B.S. in Electrical Engineering from the University of Notre Dame. Brett and his wife Susanne live on a small farm in northern Virginia in the Blue Ridge Mountains, where they enjoy the outdoors. He is a volunteer first responder and enjoys lacrosse and endurance sports, running, cycling, 70.3s, and marathons.
Selected accomplishments
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Working with Brett
Brett Jackson, Seven-time SaaS CEO, Scale-Ups, Pivots & Turnarounds Expert, is especially valuable to CEOs focused on SaaS scaling, turnarounds, and marketing and growth.
Brett Jackson's background: Seven-time SaaS CEO | Scale-Ups, Pivots & Turnarounds Expert. Deep operating experience across SaaS, Enterprise Software. That P&L perspective is what makes the coaching land.
Direct, operator-driven, and rooted in real P&L experience. Brett Jackson coaches CEOs the way a former operator coaches, focused on the decisions that actually move the business, the metrics that expose the truth, and the leadership behaviors that compound over time.
Brett Jackson is based in the United States and works with CEOs across North America and internationally through 1:1 coaching, board observation, and on-site strategic offsites as part of the CEO Coaching International team.
Companies coached by CEO Coaching International for two or more years have averaged 22.8%/yr revenue growth and 37.5%/yr EBITDA growth, roughly 2-3x U.S. benchmarks. Brett Jackson coaches to the same operating standard: measurable growth, real leverage on the CEO's calendar, and a leadership team that can execute without you.
Same rooms, different scars
Mark MosesMiami Beach, FLFounding Partner & Executive Chairman of CEO Coaching InternationalView profile 
Craig ColemanPacific Palisades, CAFormer founder and CEO with 15 years of experience building, scaling, and successfully exiting a fintech company, now coaching founder-CEOs to scale their businesses, strengthen enterprise value, and create the option for a successful exit.View profile 
Sheldon HarrisMiami Beach, FLMulti-unit operator, franchise builder, and partner on the CEO Coaching International executive leadership team.View profile 
Cynthia ClevelandLos Angeles, CAFormer Universal Studios Worldwide PresidentView profile 
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