2026 Power 100: Caitlyn Carolan

President of Worcester Restaurant Group

Title: President

Worcester Restaurant Group, in Worcester

Age: 46

Employees: 239

Carolan oversees the day-to-day operations of one of Worcester’s most prominent restaurant companies, whose portfolio includes The Sole Proprietor, One Eleven Chop House, and VIA Italian Table. Since 2025, Worcester Restaurant Group has upgraded its guest management systems, expanded off-premise dining options, and completed renovations to VIA’s outdoor patios. Her focus remains on delivering high-quality dining experiences in a city where the restaurant scene continues to evolve.

What unique skill sets you apart from others? Having worked in our restaurants since I was 13, I naturally approach decisions through the lens of the guest experience and the details that keep people coming back.

What is one habit powerful leaders should practice every day? Stay present and engaged. Strong leaders stay connected to their teams, customers, and the day-to-day details that shape culture and experience.

Why do you do business in Central Mass.? Worcester is home. We opened our first restaurant here more than four decades ago and have grown alongside the city ever since.

What is your favorite book on leadership? “Hug Your Customers” by Jack Mitchell

– Digital Partners -