An environment where talent thrives

Making a difference to our customers everyday.


Open Positions

Our Values

This is the best place to work if you're looking for an opportunity to grow professionally, in a fun, and fast-paced environment. As a fast growing company, we're always looking for dynamic individuals, self-starters and team players to join our organization.


We commit to doing the right thing all the time. When we say we’ll do something we do it.


We demand our best every day. We’re accountable and deliver beyond expectations.


Built upon an environment of mutual respect, trust, and teamwork, we have the freedom to take the initiative and to learn from our experiences.


We will not be caught off-guard as the world changes. We are continuous learners and industry thought leaders.


Not satisfied with the status quo, we evolve and adapt by being curious, agile and courageous.

Life at Sentinel Benefits

The best companies hire the best talent. As one of the largest and fastest growing employee benefits firms in Massachusetts, Sentinel Benefits is always looking for dynamic individuals to join our organization. We employ over 200 benefit professionals who serve more than 2,700 clients through the U.S. From our conveniently located offices in Massachusetts and New York, we design and manage employee benefits and provide financial and regulatory advice to businesses, individuals, and their families.

Since 1987, we've been dedicated to offering comprehensive, professional and innovative financial services. From insurance brokerage and employer benefit administration to retirement plan and investment advisory services—our clients depend on us as a trusted provider catering to their every need.

We support work/life balance.

We work hard, but we also recognize the value of balancing business with personal life. That’s why Sentinel Benefits offers a flexible work environment for our employees. Arrangements include teleworking and flexible schedules that are made with managers on an individual basis according to specific job responsibilities.

Additionally, we offer our employees the very same peace of mind we provide our clients. Our own benefits package is robust to meet the diverse needs of our employees and their families. These include:

  • Several health plan options
  • Reimbursement and health savings accounts
  • A retirement plan allowing for traditional (pre-tax) and Roth (after-tax) 401(k) contributions—and yes, there’s a match!   
  • Life and Disability Insurances
  • Competitive paid time off, summer half days and the Sentinel Recharge program for tenured employees
  • Tuition reimbursement
  • Matching charitable gift program

Culture is infectious.

We believe that corporate culture can help maximize productivity—our employees are part of a unified team who enjoy working together to reach the common company goals. We embrace an open-concept floorplan where we find collaboration and teamwork continuously thrive. We encourage growing interdepartmental relationships by connecting outside of the office at company-sponsored events (departmental kickoffs, quarterly off-sites, employee-appreciation and charitable outings and paid volunteer days, holiday parties, and more). Our people are our core and we recruit for a cultural fit that grows our team for the long-term.