Location Note: Hybrid in Wakefield, MA or Troy, MI (1-2 days per week) preferred. Role can also be remote.

The Purpose of Your Role:
We are seeking a team-oriented professional for our Operations Team. The role offers a way to work in a fun, fast-paced work environment while providing the opportunity for operationally minded individuals to begin their journey within the organization and start their career in Operations. The Operations Associate will perform a variety of functions as it relates to entry-level plan operations such as payroll processing, check issuance and distribution processing.  The ideal candidate will be able to effectively communicate, multi-task and prioritize responsibilities based on the needs of the team and clients and be a team player.    

What you'll bring to Sentinel:

• A passion for problem solving and operational thinking
• A sincere interest in working within/learning the financial services industry (if you don't have financial services experience).
• Ability to work well in a fast-paced and collaborative environment
• Detail oriented thinking

What you’ll be responsible for:

• Respond to incoming tickets from other departments
• Monitor, process, and reconcile contribution files for retirement and 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, rollovers, loan payment, and loan payoff transactions
• Perform cash reconciliation activities for our custodial partners
• Assist internal teams with responding to client inquiries
• Proficient in Microsoft Office programs and the ability to quickly learn new systems (CRMs, recordkeeping, etc.)
• Process distribution and loan requests
• Monitor status of Distribution and loan requests
• Monitor Inbox and log distribution and loan requests to Sales Logix
• Follow up with client and/or Plan Consultant on NIGO requests
• Perform QC of data in accordance with departmental standards
• Assist client service and Plan consultants in answering client inquiries
• 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
• Have successfully completed or working to complete the ASPPA RPF modules
• Salary Range: $45,000-$50,000

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).