Conversations That Matter: How To Turn Your Holiday Customers into Year-Long Customers

The holidays bring excitement and visibility—a perfect time to welcome people, showcase your best, and create lasting impressions. But real success comes from turning that moment into a lasting connection.

We'll talk with Stephen Warley, a dedicated community builder and digital media veteran, to understand instead of asking, “How do I sell?” ask, “How do I serve so well that they stay with us year-round?”

Learn Strategies to:

Deliver standout care and value during the rush so people remember you.

Follow up and engage beyond the sale—build trust, belonging, and continuity.

Offer something after the holidays: education, maintenance, memberships, events—whatever fits your business.

The goal isn’t just sales—it’s relationships. Capture the holiday surge, but think beyond it. The people you meet in December can become loyal customers in March and August. That shift—from seasonal to year-round—turns a business into a community resource.

Speaker: Stephen Warley, founder and solopreneur of Life Skills That Matter, now calls North Adams, Massachusetts, home. With a background in broadcasting and solo entrepreneurship, Stephen has turned his attention to fostering local innovation and connection in the Berkshires.

Hosted by: Tim Kiely, Senior Business Advisor, Massachusetts Small Business Development Center - Berkshire Region

Co-sponsored by The Williamstown Chamber of Commerce.