An environment where talent thrives

Our ultimate goal at Sentinel is to help people prepare for their future Health & Wealth needs. From retirement plans to group health insurance to reimbursement accounts to financial planning, we engineer solutions and then continuously strive to make them better. 

We're looking for innovators, self-starters and team players to make that happen.

Sentinel was recognized by The Boston Globe as a Top Place to Work in 2020. In 2021, 2022, and 2023 Sentinel earned Top Workplace USA Awards from Energage.

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Open Positions

Our people are our core, and we recruit for a cultural fit who can thrive with our team for the long term. Sentinel has a number of opportunities to grow professionally in a fun and fast-paced environment.
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Why Work for Us?

Top 10 reasons to work for Sentinel

  1. We believe in and practice diversity, equity and inclusion
  2. Flexible work schedules, including remote and hybrid options
  3. Generous time off policies, including unlimited Flexible Time Off (FTO) after 2 years of service
  4. Career pathing and career development
  5. Parental leave and family care programs
  6. Mental health resources
  7. Tuition reimbursement program
  8. Employee events (holiday celebrations, summer cookouts, wellness days, etc.)
  9. Free guidance from a Financial Planner who will help you with your retirement investments
  10. Sentinel Recharge (after 10 years of service, we reward employees for their hard work by offering a four-week paid sabbatical to rejuvenate)

We Live Our Values

At Sentinel, our foundational five are more than just words – they're a way of life. We understand companies with a solid culture and a higher purpose perform better. As we continue to grow, we strive to ensure that our culture remains alive and well.

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 initiative and 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.

We Love Our Communities

We are a team of people – volunteers, givers, supporters and mentors – who set out to do good in the world.
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Being in the employee satisfaction business gives us a unique perspective on designing plans to meet the needs of our employees. We are committed to offering the most progressive and comprehensive employee benefit plans available in the marketplace.

Some of our benefits include:

  • PTO (vacation, sick, personal time bank)
  • FTO (after 2 years of employment)
  • 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 3.75% employer match
  • Parental leave

We Love Our People

Without our amazing employees, Sentinel wouldn't be where it is today. Our quarterly awards honor these exceptional people!
Meet Our All-Star Sentinels
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Sales Development Representative (SDR)

Sentinel's Sales Development Representative role is unique. We've incorporated a rotation component to fully immerse our Sales Development Representatives (SDRs) into each business unit where you gain first-hand experience alongside sales professionals. This alignment is made in order to help you achieve the goal of becoming a quota carrying Sales Consultant more rapidly. 

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