Seasonal Benefits Operations Assistant

Built on meritocracy, our unique company culture rewards self-starters and those who are committed to doing what is best for our customers.

Winston Benefits, a Brown & Brown company, is seeking a Seasonal Benefits Operations Assistant to join our team!

The Seasonal Benefits Operations Assistant will provide critical support to Winston Benefits during the annual Open Enrollment period. This temporary position will assist with reporting, file tracking, and carrier communications to ensure accurate and timely execution of client deliverables. The role is expected to run from September through November, with the potential for extended hours during peak workload periods.

WHAT YOU’LL DO:

• Run daily reporting based on client and communication schedules.

• Attach reports to the issue tracker according to client requirements, schedules, and formats.

• Assign issue tracker items to the communications team.

• Send Open Enrollment (OE) questionnaires to carriers, upload responses into the issue file, and confirm alignment with Winston Benefits’ templates.

• Create and manage carrier holiday issues to remove or add files from the scheduler.

• Track new file implementations and ensure SFTP issues are created and properly linked.

• Update carrier-related issues on the punch list.

• Perform other duties as assigned in support of seasonal operations.

WHAT YOU’LL NEED:

• Strong organizational and multitasking skills.

• High attention to detail with the ability to ensure compliance with established templates and processes.

• Proficiency in tracking, documenting, and updating project-related activities.

• Effective communication and collaboration skills.

• Ability to work independently and meet deadlines in a dynamic, seasonal workload environment.

• Flexibility with work hours during peak enrollment periods.

Pay Range

22 - 28 Hourly

The pay range provided above is made in good faith and based on our lowest and highest annual salary or hourly rate paid for the role and takes into account years of experience required, geography, and/or budget for the role.

Teammate Benefits & Total Well-Being

We go beyond standard benefits, focusing on the total well-being of our teammates, including:

• Health Benefits: Medical/Rx, Dental, Vision, Life Insurance, Disability Insurance  
• Financial Benefits: ESPP; 401k; Student Loan Assistance; Tuition Reimbursement 
• Mental Health & Wellness: Free Mental Health & Enhanced Advocacy Services
• Beyond Benefits: Paid Time Off, Holidays, Preferred Partner Discounts and more. 

Not reflective of all benefits. Enrollment waiting periods or eligibility criteria may apply to certain benefits. Benefit details and offerings may vary for subsidiary entities or in specific geographic locations. 

The Power To Be Yourself  

As an Equal Opportunity Employer, we are committed to fostering an inclusive environment comprised of people from all backgrounds, with a variety of experiences and perspectives, guided by our Diversity, Inclusion & Belonging (DIB) motto, “The Power to Be Yourself”.