Behind the Benefits: How Our Dedicated Enrollment Services Team Supports You
April 15, 2025
- What are the typical services your enrollment services clients take advantage of?
Our clients take advantage of a full range of services designed to make the benefits enrollment process easier, more efficient, and more personal. That includes one-on-one support from our Licensed Benefits Counselors, bilingual assistance in over 240 languages, and a dedicated call center team. We offer multiple ways for employees to enroll; whether that’s over the phone, online, or in person, so it’s flexible and accessible for all .
We also build out strategic, client-specific communication campaigns that help employees really understand their benefits and make informed decisions, not just check a box.
Another big plus for our clients that they appreciate is that even if they’re already using a benefits administration platform they love, like Workday, ADP, PlanSource, and others, and do not want to migrate to a new platform, we’re able to jump right in and work within those existing systems. Our team has over 10 years of combined experience with most major platforms, so we can handle administrative tasks like dependent verification, enrollment management, new hire communications, and reporting. It takes a lot of the admin work off their HR team’s plate and keeps everything accurate and running smoothly behind the scenes.
- How is the call center able to help the employees with regards to their enrollments?
Our call center plays a critical role in supporting employees throughout the enrollment process. It serves as a direct, accessible resource where employees can ask questions, receive one-on-one guidance, and get help navigating their benefits. Our Licensed Benefits Counselors are trained to actually talk with employees, not just at them!
Benefits Counselors are specialists trained on each client’s unique benefit offerings and nuances, and they are available to walk employees through their options, explain complex terms in plain language, and ensure they understand the impact of their choices. We also offer support in multiple languages and accommodate different time zones to ensure no employee is left behind and can call in when their schedule allows for it. Whether someone’s a first-time enrollee or just needs help sorting through their options, we’re there to walk them through it step-by-step. It’s all about making benefits feel a little less overwhelming and a lot more human. Licensed Benefits Counselors not only guide employees through their benefits with clarity and understanding, but also work closely with our Enrollment Services Account Executives to escalate any issues and ensure nothing falls through the cracks.
- What makes Winston’s enrollment service support unique from others?
What sets Winston apart is our white-glove, high-touch, and flexible approach to service. We tailor our enrollment support to meet each client’s specific needs, ensuring both the employer and their employees receive a personalized and engaging experience. Unlike many companies, we don’t just have the ability to provide technology—we pair it with people. Our experienced Licensed Benefits Counselors deliver education and empathy, not just transactions.
Not only do we pride ourselves on working to support employees, but our Enrollment Services team will also work with the client to ensure they feel fully supported within their benefits administration platform, providing a dedicated Account Management team for ongoing support. What sets us apart really is the ability to adapt to what the client does today. We’re not asking them to change what works—we adapt to their current setup and layer in our expertise to help streamline processes, improve efficiency, offer best practices from across the industry, and take the weight off their shoulders and free up their HR team to focus on other priorities.
Plus, our flexibility in integrating with various platforms and adapting communication strategies ensures that we meet employees where they are, making the enrollment experience more intuitive and impactful. It’s all about making the enrollment and administration process easier, more personal, and more impactful for everyone involved.


