Why Winston?

Our goal: HR simplified.
Benefits delivered.

Founded in 1987, our story started with a vision and commitment to streamline the administrative demands of an HR professional. As early adopters of the automated benefits enrollment process, we brought the digital age to customers through our proprietary SaaS-based benefits technology, today called, HRally®.

Like technology, we have evolved, and today we are a benefits administration, enrollment, and employee engagement communication subsidiary of Brown & Brown Insurance.

We provide seasoned benefit specialists to 80+ clients and multiple brokers, servicing more than 1.2 million benefits plan participants.

Our continued focus is on improving outcomes and delivering value by providing each customer with a customized portfolio of benefits administration services. Our tools and solutions extend the reach and voice of Human Resources to every employee.

Our Brand Pillars


Collaboration and devotion to your business, because we’ve been there.


Experience and innovation at the forefront, with people guiding the way.


Peace-of-mind, time efficiency, and accuracy, our team owns the process.

Meet the New Winston

Our values, services, people, and mission haven’t
changed. But the way we tell our story has.

Our Team

As your HR ally, we are committed to helping you deliver benefits solutions to better execute the HR role and service the companies’ benefits needs.

Bob Bradley

Founder and Chairman

Colin Bradley

President, Chief Executive Officer, Principal

Curry Bradley

Chief Marketing Officer, Principal

Robert Wingel

Senior Vice President of Business Operations

Craig Butler

Senior Vice President of Enrollment Services

John Russotto

Chief Technology Officer

Alicia Greco

Vice President of Service Delivery

AJ McFadden

Director of Customer Experience

Duane Walcott

Vice President, Enrollment Services

Kristen Rizzo

Manager of Account Services

Linda Ramsden

Vice President of Human Resources

Dennis Young

Director of Software Development