An Environment Where Talented Individuals Thrive

The best companies hire the best talent. As one of the largest and fastest growing employee benefits firms in Massachusetts, Sentinel Benefits & Financial Group is always looking for dynamic individuals to join our organization.

Our Values

Expertise – Strive to be industry thought leaders through innovation and experience. Be a continuous learner.

Commitment to Excellence – Take ownership for commitments made and deliver beyond expectations.

Empowerment – Be empowered, take the initiative.

Integrity – Do the right thing by making the right decisions for the client and the company.

Celebrating our success and rewarding our employees is also an important part of our corporate culture. We are committed to attracting and retaining a talented workforce – which is why we offer a comprehensive benefits package.

If you’re looking for an opportunity to grow professionally, in a fun, fast-paced environment – it may be time to start thinking about building a rewarding and challenging career at Sentinel Benefits & Financial Group.

Open Positions

We are looking for self-starters and team players that have a passion to build a career in a fast-paced working environment.

Since our inception in 1987, Sentinel Benefits & Financial Group has been dedicated to offering comprehensive, professional and innovative employee benefits services to thousands of businesses throughout the United States including Retirement Plan Design, Administration and Compliance. Other benefit services include Flexible Spending Accounts, and COBRA Administration and Group Insurance Brokerage & Advisory Services.

If you have experience in any of the areas listed above, Sentinel may have a position for you. Some examples of the types of positions that support our business are:

  • Insurance or Securities Sales Representative
  • Pension/401(k) Administrator
  • Client Relationship Manager
  • Service Representative
  • Electronic Payroll Processing Associate

We employ over 200 benefit professionals who serve more than 2,700 clients throughout New England and the U.S. From our conveniently located offices in Massachusetts and New York, you will enjoy a team-oriented work environment. Recognized as one of the largest privately owned benefits firms in Massachusetts, we’re always looking for the right people to join our team. 

To Apply

If you are interested in a career at Sentinel, please submit your resume and a cover letter to the email address provided below. Candidates selected for interviews will be contacted within two to three weeks of the date of submission. If you do not hear from us at that time, your resume will be kept on file for one year should an opportunity that matches your skills and experience become available. 

Email your resume to:

Employee Benefits

Being in the employee satisfaction business gives Sentinel Benefits & Financial Group a unique prospective on designing plans to meet the needs of our employees. We are committed to offering the most progressive and comprehensive benefit plans available in the marketplace. Here are some of the highlights.

A Special Place to Build a Career
To be successful in any business, a great company must create a work environment that fosters pride in its accomplishments and service as well as trust, mutual appreciation and teamwork among its employees. To build these types of relationships, employees must get to know and respect each other. They must genuinely care about the success or failure of each person with whom they work. Sentinel Benefits & Financial Group’s work environment is such a place. Our people find more than just employment: they find people worth knowing who care about their futures and are concerned with the success of the business they are helping to build.

Celebrating Success
Our company meetings provide for an opportunity to learn about our business, celebrate our successes and interact with other departments over lunch. In addition to our company meetings, we also encourage non-business celebrations such as our ice cream socials, summer outings and holiday parties.

Helping People Prepare for Retirement Is Our Business
At Sentinel, retirement planning is a primary concern. We believe that it is our responsibility to help our employees build the future they want and deserve. That’s why we offer a 401(k) plan with an annual discretionary match and Profit Sharing contribution.

Sentinel also provides an investment program that offers the industry’s best investment managers for each investment class. The program focuses on asset allocation for long-term performance. For employees who do not wish to pick their own funds, Sentinel’s plan offers LifeStyle choices. These “fund-of-funds” are actively managed by our own professional advisors.

Great Healthcare Means Peace of Mind
We offer three health plans from Blue Cross Blue Shield to meet the diverse coverage and budget needs of our employees. Employees can choose a traditional HMO or PPO plan or an HSA eligible PPO plan depending on their individual needs. Our HMO plan requires only a 30% contribution from employees for both individual and family coverage. Of course, all employee contributions to the plan are made on a before-tax basis.

Flexible Spending Accounts
As a leading administrator for FSA plans, we are pleased to offer this benefit to our employees. FSAs allow employees to pay for unreimbursed healthcare expenses on a pre-tax basis. In addition to healthcare, employees can also pay up to $5,000 per year for dependent care expenses as well.

Life and Wage Protection
As one of the region's largest benefits brokers, Sentinel Benefits & Financial Group understands risk and knows that while death and disability happen infrequently, these events create devastating financial issues for families. That is why we offer and pay 100% for our employees’ Life, Accidental Death & Dismemberment, Short Term and Long Term Disability insurance coverage.

Time off from Work
We work hard and recognize that time off is important to rejuvenate the mind and body. That is why we offer a progressive vacation policy to our employees. The longer you are employed by Sentinel, the more time off you accrue. In addition to scheduled vacation time, we also offer 9 paid holidays and 1 paid floating holiday per year.

Our benefits provide a substantial addition to our compensation package as well as keeping us competitive in the marketplace. For additional information, please contact us