Jerry Swain.

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.

Jerry is especially effective with founder-led and entrepreneurial companies that need to professionalize without losing their scrappy edge. His work often focuses on building a stronger sales engine, improving cash flow and profitability, aligning the leadership team, creating accountability rhythms, and preparing the business for long-term scale or eventual exit.

His clients often come to him when they are stuck in a revenue plateau, rebuilding a sales team, struggling with cash flow, preparing for growth, or trying to turn entrepreneurial energy into a more disciplined operating company.

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. As the longtime Chair of a TIGER 21 group in San Diego, Jerry brings a deep appreciation for peer learning, candid conversations, and the power of trusted relationships among accomplished entrepreneurs and business leaders.

Jerry also leads CEO Coaching International’s Sales Excellence Program, an intensive 8-week program designed to help CEOs, founders, sales leaders, and sales professionals build a repeatable sales process, strengthen discovery and qualification, improve objection handling, practice through live role play, and create a sales playbook they can use immediately.

Jerry also facilitates CEO Coaching International’s Entrepreneurial Mastermind Group (EMG), combining one-on-one coaching, peer learning, and accountability to help founders of smaller companies navigate the challenges of growing and professionalizing their businesses.

Jerry has a deep zeal for life and is known for bringing warmth, humor, and a smile into the rooms he enters. He is the author of Tell Me Something Sweet, a book of chocolate-inspired quotes, with proceeds donated to charity. After a recent health challenge, Jerry brings an even deeper appreciation for relationships, resilience, and living with purpose. He is also a proud father of two and enjoys music, sports, and connecting with people in meaningful ways.

Areas of focus
Sales Excellence • Sales Team Development • Founder-Led Companies • Entrepreneur Coaching • Cash Flow and Profitability • Leadership Team Alignment

Listen to Jerry Swain’s podcast episodes, The 6-step process that leads to BIG sales with CEO Coaching’s Jerry Swain and A 4-step process for developing a world-class sales team