Our Team

Winters-Oliver Core Values


We build trust by operating in an honest and direct manner.


We remain informed, educated, and prepared to efficiently serve our clients in an ever-changing world.


We provide a client experience that exceeds expectations by being proactive and efficient.

Meet the Team

Ben Winters, CIC

Agency Principal & Commercial Lines Risk Advisor

(804) 417-9247

Sherwood Bowditch

Agency Principal & Commercial Lines Risk Advisor

(804) 417-9248

Andrew Farrar

Commercial Lines Risk Advisor

(804) 417-9245


Jennifer Naquin

Employee Benefits Account Manager

(804) 522-1326

Yvonne Ryan, CISR

Director of Service & Operations

(804) 417-9241

Mary Ann Sisson, CIC

Commercial Lines Account Manager

(804) 417-9243

Abby Parks, CISR

Commercial Lines Account Manager

(804) 997-4019

Catie Allen

Commercial Lines Account Manager

(804) 417-9242

Cody Coletta

Personal Lines Account Manager

(804) 417-9244

Alaina Warren

Administrative Assistant

(804) 746-5178 x361