Trailblazers Round Table 2026

Endeavor Trailblazers Round Table

April 28, 2026

Step into a room full of wisdom, leadership, and opportunity at the Trailblazers Round Table — happening at the beautifulCountry Club of Winter Haven.

This one-of-a-kind experience gives professionals the chance to rotate tables every 8 minutes with some of our community’s most impactful leaders. You’ll hear real stories about career growth, daily habits, hardships, and major accomplishments — all while asking your own questions and making meaningful connections.

Meet the 2026 Trailblazers:

• Steve Lester- Chief of Staff, Polk County Sheriff's Office
• Maria Cruz- Executive Director, Talbot House Ministries
• Steve Warner- Vice President for Resource Development and Executive Director of the Polk State College Foundation , Polk State College
• Rachelle E. Williamson- Judge, The Courts of the Tenth Judicial Circuit
• Stephen Kalogridis- Managing Partner, Silver Properties of Winter Haven, LLC
• Amy Sexson- Partner/Editor, Destroyer Media and Marketing, LLC

Location: Clubhouse at the Country Club of Winter Haven (2nd Floor Dining Room)

⏰ 5:00 PM – 8:00 PM (Round Table begins at 6:00 PM)

Catered by the Country Club of Winter Haven

Whether you’re building your career or elevating your leadership, this event is designed to help you grow, connect, and gain powerful insight from those who have paved the way.

Members: $25

Non-Members: $45

✨ Seats are limited — everyone is welcome, so secure yours today!