30+ Years at Sentinel: Rob DiMase

In this Sentinel Spotlight series, we're excited to introduce some of our longest-tenured employees! This week, get to know Rob DiMase, one of our Partners. We asked Rob about his experiences over the past 30+ years, and he shared some great advice for someone starting their career at Sentinel Group.

Over the years, Sentinel Group has grown and evolved—what are some of the biggest changes you’ve witnessed, and how have they shaped your experience? 

I've had the privilege of watching Sentinel grow from a single office with fewer than 10 employees—primarily serving clients in Massachusetts—to a national firm with over 250 associates and a footprint across the U.S. I was fortunate to join the firm at the ground level and was given tremendous opportunities to grow alongside it. 

Early on, I was involved in key strategic decisions, including acquisitions, real estate expansion, and the development of new product offerings. Over the years, I’ve worn many hats—from wholesaling our Health & Welfare and Retirement Plan Services to retail sales of our institutional offerings. I’ve served as Director of Finance (with a sales goal, no less), President of the insurance agency, and Head of Sales. I even, somewhat reluctantly, ventured into wealth management at my father-in-law’s request—and now maintain a small book of friends and family clients. 

I’m grateful for the diverse experiences I’ve had and am committed to creating similar opportunities for other driven, entrepreneurial team members. 

Sentinel Group is known for its strong culture of employee retention—what do you think sets the company apart and keeps employees engaged for decades?

In addition to the growth opportunities I mentioned earlier, I think what truly sets Sentinel apart is the strong sense of family and the diverse nature of our work. It’s a place where people feel connected and supported—where relationships matter. On top of that, the variety in what we do keeps things fresh. I rarely find myself bored, and if I ever feel like I'm in a rut, there's always a new challenge or area of the business where I can contribute and make an impact. 

For someone just starting their career at Sentinel Group, what advice would you give to help them succeed and build a long-term future here? 

To succeed at Sentinel and build a long-term future here, come in with a strong sense of curiosity and a genuine desire to be a lifelong learner. The most successful people here are the ones who ask questions, seek out new experiences, and stay open to growth throughout their careers. 

The industry has changed significantly over the past few decades—what are the biggest shifts you’ve seen, and how has Sentinel Group adapted to stay ahead? 

While the industry has certainly evolved, it’s felt more like a steady progression than a sudden shift. At Sentinel, we've always taken pride in staying ahead of trends and adapting our offerings to meet the changing needs of the market. We were early adopters of the "health, wealth, and retirement" approach, long before it became an industry buzzword. Unfortunately, we didn’t have the same platform as some of our larger competitors to amplify our message, but our commitment to integrated, client-focused solutions has always been ahead of the curve. 

Job loyalty has become less common in recent years. What about Sentinel Group has inspired you to stay for [X] years, when many others change jobs frequently?  

I was fortunate to join Sentinel early in its journey and was given meaningful opportunities to make an impact from a young age. I had incredible mentors who supported me every step of the way, and I became a partner in my late 20s. That level of trust and investment in my growth created a strong sense of loyalty. Just as importantly, I’ve rarely felt bored—there’s always a new challenge to take on, a way to add value, and a chance to make a difference for our clients. That constant evolution is what’s kept me engaged all these years