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Benefits Implementation & Education Specialist

Location:
Chicago, IL
Posted:
January 04, 2026

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Resume:

SHELBY CONDON

Hebron, Illinois *****

815-***-**** **********@*****.*** https://www.linkedin.com/in/shelbylcondon/

SUMMARY

Experienced Benefits Specialist with a strong background in administering voluntary benefit plans. Skilled in guiding clients through annual open enrollment, qualifying life events, and day-to-day benefits inquiries focusing on accuracy, clarity, and compliance. Adept at interpreting and applying benefits regulations, including ACA, COBRA, HIPAA, and ERISA, to ensure adherence and reduce risk. Proven ability to manage carrier relationships, facilitate file feeds and eligibility audits, and support HRIS and benefits platform implementations. Known for delivering effective employee education, troubleshooting complex benefits issues, and maintaining high levels of client satisfaction in fast-paced environments.

EXPERIENCE

bswift, Remote

FSA Implementation Manager, 2025-present

●Worked directly with clients to implement new, full benefit implementations. Anticipated client needs and addressed concerns when presented.

●Provide leadership and recommendations to team members to maintain necessary deadlines.

WEX, Remote

FSA Implementation Manager, 2023-2025

●Communicated with new and existing clients to set up FSA implementations. Maintained close relationships while implementing the plans, working to anticipate any needs or concerns for clients, remaining available to them consistently during and after implementation to offer consistent and confident support and information.

●Maintained a consistent meeting schedule and project plan to ensure both the client team and internal team felt confident and comfortable with the progress being made, with frequent check-ins to identify any concerns or questions immediately.

●Identified important requirements to meet standards, both for the benefits setup and ongoing client satisfaction. Maintained a high level of client satisfaction, ensuring the clients were confident in abilities once the active administration process began.

●Provided training and updated training documentation and reference documents for FSA and claims teams. Built custom processing procedures as necessary and provided them to the clients and teams, encouraging any questions or suggestions for making these documents more efficient and useful for their needs. In doing so, ensured open availability to the client and team to ensure the processes were successful and operated with a high level of success.

●Coordinated regarding special client requirements and communicated with external client teams and independent vendor teams for client satisfaction. Identified any potential pain points or difficulties before implementation to appropriately address them before active administration. By showing an understanding of unique requirements for clients, dramatically decreased manual processing time and potential errors and increased client confidence in staff knowledge and skill level.

WEX, Schaumburg, Illinois

FSA Administrator, 2016-2023

●Processed reimbursements from flexible spending accounts and ensured processes were in compliance with IRS regulations. This required being knowledgeable about guidelines and eligibility information and ensuring we upheld the necessary standards for the accounts.

●Responsible for building and providing reports to clients. Worked with clients who required specialized reporting to ensure the best possible options were provided and any concerns regarding their standards were answered.

●Applied and audited payroll records for clients and identified any errors in the records received, ensuring system was updated correctly and ensuring client confidence.

●Worked with clients as their direct contact to ensure their records were correct, provided requested information, and made any necessary changes. Served as the first line of contact and worked to troubleshoot any problems or concerns in order to better serve clients.

NORTHERN ILLINOIS UNIVERSITY, DeKalb, Illinois

Research Assistant, 2014-2016

●Conducted over 200 interviews with individuals regarding detailed, sensitive topics, working with them to get the fullest response and encouraging them to feel confident.

●Handled delicate situations and information and worked with individuals to ensure they felt supported and comfortable throughout the experience. Interviewees would leave the discussion confident their information was secure and with a positive perspective on the time spent.

●Helped utilize the data collected through this process to build a detailed research project. This included transcribing the interviews, making detailed notes, and occasionally reaching out again for additional discussions with the interviewees.

ADDITIONAL EXPERIENCE

SYMBRIA RX SERVICES, LLC, Woodridge, Illinois, Data Collection Specialist, 2015. Collected relevant data for ongoing study regarding benefits of specific medication distribution systems. Conducted the research in active work environments and learned how valuable it is to be adaptive when the environment requires it. Successfully encouraged the project managers to alter their collection requirements after identifying potential issues that had not been previously noted, which ensured the study was more accurate and provided better data.

HAPPY JACK’S, McHenry, Illinois, Assistant General Manager, 2007-2015. Supervised and oversaw daily operations, such as managing and training staff, ensuring customer satisfaction, and maintaining food safety standards. Maintained a positive work environment and guaranteed customers were satisfied with their experiences. Developed interpersonal skills and helped understand the many different ways people learn and communicate, which was implemented in training.

EDUCATION

NORTHERN ILLINOIS UNIVERSITY, DeKalb, Illinois

Master of Arts, Sociology

NORTHERN ILLINOIS UNIVERSITY, DeKalb, Illinois

Bachelor of Arts, Sociology

MCHENRY COUNTY COLLEGE, Crystal Lake, Illinois

Associates of Science

TECHNICAL SKILLS

Microsoft Office Suite (proficient in Excel), Google Suite, Workday, EDI file proficiency, Secured Data Networks, Benefits Administration Platforms, Data Analysis & Reporting, Compliance Knowledge (ACA, COBRA, HIPAA, ERISA, IRS guidelines for FSAs), Documentation and Training, Communication and Support Tools



Contact this candidate