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About Our Company

For 30 years, Winston Benefits has been Connecting People with Benefits. 

Founded in 1987, Winston had a vision to help our clients simplify the complexities of open enrollment, streamline the administration of their benefit plans, and develop strategic communications to improve employee engagement.

As early adopters of the automated enrollment process, we brought the digital age to our clients by helping them migrate from paper enrollment processes to electronic solutions.

Like technology, we have evolved over time.

Today, we are a privately owned Benefits Administration, Enrollment and Communication company. Our team continues to deliver innovative solutions to clients to help them manage, enroll and administer their benefit plans. We have one simple goal: Connect People with Benefits!

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Why Winston

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Innovative

Delivering innovative solutions to help you manage your benefits.

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Engaged

Keeping employees engaged and helping them make better benefit decisions.

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RESPONSIVE

Supporting our clients through multiple channels that fit unique employer and employee needs.

OUR CLIENTS

Winston partners with over 80 clients and multiple brokers to serve more than 1.2 million plan participants.

We combine the business models of several different vendor types to deliver a suite of integrated benefit management tools that meet unique business needs.

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Client Testimonial

  • "Everyone worked together to serve as an extension of our HR team. The educational tools and daily and weekly communications ensured employees were reached and and engaged."

    VP of Compensation & Benefits at a Health Diagnostics Company

OUR TEAM

Working together, we offer you the knowledge, expertise and experience to deliver innovative solutions that meet your HR and benefit needs.

 

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Bob Bradley
Founder and Chairman
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Colin Bradley
President, CEO and Principal
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Curry Bradley
Chief Marketing Officer and Principal
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Craig Butler
Senior Vice President  of Enrollment Services
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Linda Ramsden
Chief Human Resources Officer
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John Russotto
Chief Technology Officer
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AJ McFadden
Director of Customer Experience
 
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Alicia Greco
Vice President, Service Delivery
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Tanya Gappy
Vice President, Employer 
West
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Eamonn Brady
Vice President, Employer Solutions
Northeast
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David Blum
Vice President, Employer Solutions
Midwest
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Michael Umpleby
Vice President, Employer Solutions
Southeast
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Duane Walcott
Vice President, Enrollment Services
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Keith Walden
Senior Account Manager
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Speak with a solutions consultant today! Get Started