We are seeking a team-oriented professional for our FSA Operations Team. The FSA Operations Analyst will perform a variety of functions as it relates to entry-level plan operations such as contribution payroll processing, eligibility/enrollment file processing and other daily tasks related to the business needs. The ideal candidate will be able to effectively communicate, multi-task and prioritize responsibilities based on the needs of the team, clients and vendors.
What you'll bring to Sentinel:
- A passion for problem solving and operational thinking
- A sincere interest in working within the financial services industry
- Ability to work well in a fast-paced and collaborative environment
- Detail oriented thinking
- Monitor, process, and reconcile contribution files for reimbursement plans through our recordkeeping systems
- Monitor, process, and reconcile eligibility/enrollment files for reimbursement plans through our recordkeeping systems
- Initiate funding requests (ACH) and reconcile received deposits for plan contributions
- Generate and review various contributions reports
- Process and post participant contributions transactions
- Assist internal teams with responding to client inquiries
- Proficient in Microsoft Office programs and the ability to quickly learn new systems (CRMs, recordkeeping, etc.)
- Monitor Inbox and log certain requests in the CRM
- Follow up with client and/or Account Managers on NIGO requests
- Perform other duties and participate in special projects as assigned
About you:
We are looking for innovative thinkers to drive our business forward—someone with an entrepreneurial spirit, customer focus, drive, determination, and the strength of character to challenge the status quo. The financial services industry is forever changing and we are looking for someone who is flexible and willing to embrace change.
Preferred qualifications:
- Proven ability to take initiative and be a self-starter in handling issues
- Excellent verbal and written communication skills
- Demonstrated ability to consistently deliver a superior level of productivity and quality service
- Demonstrated organizational skills and ability to manage multiple priorities
- Ability to work in a team environment
- Ability to track and meet deadlines
- Proficiency in MS Office
- Knowledge of FSA/HRA/HSA plans
At Sentinel, compensation is calibrated to your geographic location to reflect local market conditions; the posted salary range may vary based on where you live.
What you’ll be part of:
Joining our company means becoming part of something special. We're driven by a mission to excel in our industry and within our team, supported by people who truly care about our organization.
Sentinel was recognized by The Boston Globe as a Top Place to Work in 2020, 2023, and 2025. The firm also earned the Top Workplaces USA Award from Energage through 2021-2026.
At Sentinel, we welcome people from diverse experiences, backgrounds, and perspectives – and we wouldn’t have it any other way. So even if you don’t meet every single requirement, please consider applying if you like what you see. Our priority is to find talented individuals who enrich our team culture, contribute with enthusiasm, and are passionate about what they do.
Sentinel is an equal opportunity employer and welcomes everyone to our team. If you need reasonable adjustments at any point in the application or interview process, please let us know.
Some of our Benefits:
- PTO (vacation, sick, personal time bank)
- FTO (Flexible time off for vacation, sick, and personal time) after 2 years of service
- 12 Paid Holidays (10 stated and 2 floating holidays)
- 2 Community Volunteer Days
- 5 Summer Half Days
- Medical, Dental, Vision
- Life Insurance
- LTD & STD
- Retirement Plan with 4% Employer Match
- Parental Leave
See What We Stand For: https://www.sentinelgroup.com/About-Us/Join-Our-Team
Who we are:
Sentinel Group proudly serves nearly 5,000 clients throughout the U.S. For 35+ years, we’ve remained devoted to positively impacting the lives of our people, our clients and our communities. With a 9-year average associate tenure among our 265 professionals, our team’s commitment to excellent service has positioned Sentinel as the only provider who makes benefits EASY: easy for your people; easy for your business; and easy for you.
Our ultimate goal is to help companies and their employees prepare for their future health, wealth and retirement needs. Whether it’s through retirement plans, group health insurance, reimbursement accounts or financial planning, we engineer simple solutions and continuously strive to make them better. Our in-house experts – and their commitment to excellence – define who we are.
Sentinel is also one of the largest employee benefits firms in Massachusetts (Boston Business Journal) and was named a 2022 Retirement Plan Adviser of the Year in the Mentorship category (PLANADVISER Magazine).
Skills Required
- Ability to take initiative and independently handle issues
- Excellent verbal and written communication skills
- Ability to consistently deliver productivity and quality service
- Strong organizational skills and ability to manage multiple priorities
- Ability to work effectively in a team environment
- Ability to track and meet deadlines
- Proficiency in Microsoft Office programs
- Knowledge of FSA, HRA, and HSA plans
What We Do
Sentinel Group is a single resource to manage all employee benefits. Founded in 1987, we have grown to be the second largest benefit consulting and administration practice in Massachusetts. Our services include: WEALTH PLANNING SERVICES > Investment Advisory Services > Retirement Plan Administration > Open Architecture Retirement Plan Recordkeeping > Defined Benefit & Cash Balance Plan Services > Actuarial Consulting > Employee Stock Ownership Plans LIFE PLANNING SERVICES > Group Benefits Brokerage > Flexible Spending Account Administration > Health Reimbursement Plan Administration > Health Savings Accounts > Transportation Plan Administration > COBRA Administration At Sentinel Benefits & Financial Group, we have been putting our clients first for more than two decades. In fact, building meaningful relationships with our clients to help them achieve their goals is the work we do. What differentiates us from competitors is how we approach our work. The business of providing employee benefits and financial services is not unique. There are many choices. However, brand and experience alone do not always translate to the best solution. We recognize that the only way to truly help a client is to know them first. We take the time to listen before we make recommendations. Through our interactive consulting process, we bring true custom solutions that deliver value to our clients.
