Location Note: Hybrid in Wakefield, MA or Troy, MI (1-2 days per week), or remote.
The Purpose of Your Role:
We are seeking a team-oriented professional to join our Operations Team as an entry-level Operations Associate. This role provides an opportunity to build a career in operations while learning and supporting core Inflow processes, including payroll processing, rollover processing, and loan payoff transactions.
In addition to completing daily operational work accurately and efficiently, you will be expected to ask questions, identify opportunities to improve processes, and contribute to team projects that help create capacity and improve the quality and timeliness of our work.
What you'll bring to Sentinel:
- A passion for problem solving and operational thinking.
- A sincere interest in learning about the financial services industry and retirement plan operations.
- A willingness to learn new systems, processes, and technologies.
- The ability to work well in a fast-paced, collaborative environment.
- Strong attention to detail and a commitment to accuracy.
- A proactive mindset and willingness to take initiative when you identify an issue or opportunity.
- An interest in finding practical ways to improve processes, reduce rework, and create capacity for the team.
Payroll, Rollover, and Loan Payoff Operations
- Monitor, process, and reconcile payroll files for retirement plans through our recordkeeping systems.
- Initiate funding requests, including ACH transactions, and reconcile received deposits for payroll contributions.
- Generate and review payroll reports.
- Process and post payroll contributions, rollover transactions, and loan payoff transactions.
- Perform cash reconciliation activities for our custodial partners.
- Monitor, research, and respond to internal and external inquiries regarding Inflow transactions.
- Perform quality control reviews of data in accordance with departmental standards.
- Review work carefully to identify discrepancies, missing information, and potential errors before they affect downstream teams or clients.
- Investigate routine issues, ask clarifying questions, and escalate items that require additional support or judgment.
- Maintain accurate records and complete work within established service levels and deadlines.
- Collaborate with teammates and internal partners to resolve issues and keep work moving forward.
- Keep teammates and internal partners informed about items that may affect payroll processing, rollover processing, or loan payoff work.
- Ask for help or a second set of eyes early when a plan, file, or process is unclear or unusual.
- Share relevant process updates, plan-specific instructions, and lessons learned so the team can prevent repeat issues.
- Look for opportunities to improve processes, reduce rework, create capacity, and improve the quality and timeliness of operational work.
- Take initiative in identifying issues and proposing practical solutions.
- Contribute ideas and participate in special projects, testing, process documentation, and other department initiatives as assigned.
- Support the team as processes, systems, and responsibilities evolve.
We are looking for an innovative and dependable team member who is customer-focused, motivated, and willing to contribute beyond the immediate task at hand. You are comfortable learning new information, managing competing priorities, and asking questions when something is unclear. You look for ways to improve how work gets done while maintaining a strong focus on accuracy, quality, and service.
The financial services industry is continually changing, and you are flexible, curious, and willing to embrace new systems and processes. You understand that operational excellence requires both consistent execution and a willingness to help the team improve.
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 effectively in a team environment
- Ability to track and meet deadlines
- Proficiency in Microsoft Office programs and the ability to quickly learn new systems, including CRMs and recordkeeping platforms
- Have successfully completed or working to complete the ASPPA RPF modules
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
- Passion for problem solving and operational thinking
- Interest in learning about financial services and retirement plan operations
- Willingness to learn new systems, processes, and technologies
- Ability to work effectively in a fast-paced, collaborative environment
- Strong attention to detail and commitment to accuracy
- Proactive mindset and willingness to take initiative
- Interest in process improvement, reducing rework, and creating team capacity
- Ability to take initiative and be a self-starter when handling issues
- Excellent verbal and written communication skills
- Ability to consistently deliver high productivity and quality service
- 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 and ability to quickly learn CRM and recordkeeping platforms
- Successfully completed or currently working to complete ASPPA RPF modules
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.
