Jerry Swain

Successful Retail Entrepreneur and Tiger 21 Chair 



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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.

Business Highlights:

  • Recognized by IBM as a top sales producer after completing their world-class sales training program.
  • Implements his own sales training classes and workshops for companies and corporations.
  • Extensive experience in growing CPG as well as service products with unique sales strategies, including creating or replenishing sales teams and managing extensive broker networks.
  • Has a history of increasing revenue and profit growth with sluggish products and services.
  • Strategically developed the brand, Jer’s Chocolates, creating an internationally recognized premium luxury brand recognized by The Food Network, Rachael Ray, QVC, The Home Shopping Network, and numerous local and national networks including ABC, NBC, CBS, and FOX.
  • Managed brands and manufacturing plants for seven National chocolate companies.
  • Helps companies to build and sell and create healthy cash flow.

Jerry sits on several business and advisory boards and is the current Chair for TIGER 21 in San Diego. He has been active in volunteering time and giving back in multiple ways to worthy non-profit organizations and associations, including serving on the Board of Directors for the American Cancer Society, San Diego Food Bank, and UCR Alumni Association, as well as Jer’s Cares Initiative, where his previous business committed to giving back and raised more than $250,000 for worthy charities and nonprofit associations.

Jerry enjoys fitness and spending time with his children and friends.  He is an ice cream enthusiast, collecting ice cream memorabilia. Jerry authored a gift book of chocolate quotes called “Tell Me Something Sweet,” and he donates 100% of the proceeds from the book to charity. Jerry has a passion for life, people, and balance and continues to look for ways to bring a smile to everyone he meets.

Featured Podcast:

Listen to Jerry’s podcast episode, “The 6-Step Process That Leads to BIG Sales