
Successful Retail Entrepreneur and Tiger 21 Chair
The operator behind the coach
Jerry Swain is a highly accomplished, results-driven Chief Executive Officer with over 25 years of experience in executive leadership, planning, strategy, and business operations. Jerry began his career at IBM. There, he had an award-winning career as he developed a disciplined foundation for finance, strategy, expert sales skills, and operations.
Jerry founded Jer’s Chocolates in 2004 by following a dream with a purpose, building the gourmet specialty brand from concept to a profitable international company. Jer’s Chocolates earned national recognition for its award-winning products, Jer’s inspirational story, and Jer’s Cares Non-Profit Initiative. With his successful sale of the company in 2016, he has found a new passion for coaching CEOs and executive teams.
Jerry has a unique blend of corporate pedigree and entrepreneurial grit and drive. He prides himself on his ability to understand corporate systems and processes as well as the scrappy determination and problem-solving necessary for building and selling a company.
As a coach, Jerry excels at working with founder-led companies that are looking to build and sell or are stuck in a plateau and looking to get to profitability. His approach centers on partnering with the founder to create a clear and focused plan that will drive revenue and profit growth while maintaining their passion for the business. Jerry is a collaborative leader with an inspirational style that encourages performance and sustains accelerated growth. With experience in Vistage and EO, Jerry is passionate about learning from other outstanding talented individuals.
Selected accomplishments
We pressure-test one decision you’re sitting on
Working with Jerry
Jerry Swain, Successful Retail Entrepreneur and Tiger 21 Chair, is especially valuable to CEOs focused on brand strategy, sales acceleration, and international expansion.
Jerry Swain is a highly accomplished, results-driven Chief Executive Officer with over 25 years of experience in executive leadership, planning, strategy, and business operations. Jerry began his career at IBM. There, he had an award-winning career as he developed a disciplined foundation for finance, strategy, expert sales skills, and operations.
Direct, operator-driven, and rooted in real P&L experience. Jerry Swain 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.
Jerry Swain 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. Jerry Swain 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
Don SchiavoneHudson, MASaaS Expert, Successful Entrepreneur And Operations LeaderView profile →
Mark MosesMiami Beach, FLFounding Partner & Executive Chairman of CEO Coaching InternationalView profile →
Craig ColemanPacific Palisades, CAFinancial Industry Disruptor & Entrepreneur | Over a 20-year period, Craig has built and grown successful companies in both the finance and payment processing industries.View profile →
Sheldon HarrisMiami Beach, FLMulti-unit operator, franchise builder, and partner on the CEO Coaching International executive leadership team.View profile →




NEWSLETTER
A free weekly newsletter for growth-focused CEOs, strategy, exits, and what's actually working.
Unsubscribe anytime. We never share your email.
Request a session
Tell us where to reach you and when, we’ll route you to the right coach.
By submitting you agree to be contacted by CEO Coaching International. No spam. Confidential.