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An environment where talent thrives

We help businesses and individuals think about their employee benefits and financial goals holistically.

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

35 Years of Company History

Visit our milestones
240 Employees
9.5 Years Average Associate Tenure
3 Locations

Find Your Path.

Find Your Path.

Find Your Path.

What we stand for

We live our values.

At Sentinel Benefits 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.
Integrity
We commit to doing the right thing all the time. When we say we’ll do something we do it.
Excellence
We demand our best every day. We’re accountable and deliver beyond expectations.
Empowerment
Built upon an environment of mutual respect, trust, and teamwork, we have the freedom to take the initiative and to learn from our experiences.
Expertise
We will not be caught off-guard as the world changes. We are continuous learners and industry thought leaders.
Innovation
Not satisfied with the status quo, we evolve and adapt by being curious, agile and courageous.

The behaviors our values are built on.

Learn more about what we stand for

Life at Sentinel

See what our people have to say.

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.

 

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.

Clambake 2018

Clambake 2018

Clambake 2018

Clambake 2018

Clambake 2018

Clambake 2018

Clambake 2018

Clambake 2018

Clambake 2018

Sentinel Benefits & Financial Group corporate headquarters in Wakefield, MA

Sentinel Benefits & Financial Group corporate headquarters in Wakefield, MA

Sentinel Benefits & Financial Group corporate headquarters in Wakefield, MA

Sentinel Benefits & Financial Group corporate headquarters in Wakefield, MA

Fitness Center

Sentinel Benefits & Financial Group corporate headquarters in Wakefield, MA

Sentinel Benefits & Financial Group corporate headquarters in Wakefield, MA

Balloon release to remember John A. Carnevale

Field Day 2017

Field Day 2017

Field Day 2017

Field Day 2017

Get to know our All-Star Sentinels!

EMPLOYEE AWARD WINNERS

The Boston Globe Names Sentinel Benefits & Financial Group a Top Place to Work for 2020

Top Places to Work recognizes the most admired workplaces in the state voted on by the people who know them best—their employees. The survey measures employee opinions about their company’s direction, execution, connection, management, work, pay and benefits, and engagement. 

Why work for us?

Top 10 reasons to work for us

  1. Sentinel Recharge (After 10 years of service, we reward employees for their hard work by offering a four-week paid sabbatical to rejuvenate.)
  2. We believe in diversity, equity and inclusion
  3. Workplace workouts with a professional trainer 2x per week
  4. Flexible work schedules, including remote and hybrid possibilities
  5. Career pathing and career development
  6. Parental Leave Program
  7. We wear jeans five days a week
  8. Tuition Reimbursement Program
  9. We host employee events such as holiday parties, summer cookouts, wellness days throughout the year
  10. Get free guidance from a Financial Planner who will help you with your retirement investments

Open positions

Opportunities to grow professionally in a fun and fast-paced environment.

View Open Positions
How to Apply
If you are interested in a career at Sentinel...
Send us your resume and cover letter
Benefits
Being in the employee satisfaction business gives us 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.
Learn more about our benefits

Not quite ready to make a move? Stay connected when new jobs post.

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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. 
Learn more

SentinelCares

We Love Our Communities

We are a team of people--volunteers, givers, supporters, and mentors--who have set out to do good in the world.
Learn more about SentinelCares

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