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How We Got Here

We know employee benefits. That’s what we do. Not just medical insurance but the entire range of coverages including dental, vision, life, disability and voluntary coverages.

But what distinguishes Stillwater Benefits is our focus on smaller employers. Whereas most brokerage firms concentrate on large employers, our attention is on businesses with 2 to 100 employees. This commitment to smaller businesses means 3 things to our clients:

  1. We provide personalized service – we see our clients during the year no matter their size;
  2. We know our products – We know “what’s under the hood” and this helps us recommend the best insurance solution for our clients;
  3. We provide big company benefits for small business – In essence, we become your HR resource delivering personalized attention

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Although Stillwater Benefits is relatively young, (established in 2015) our founder, Steve Roberts, has considerable experience in the industry. In 2001, Roberts launched Orca Bay Benefits with a similar focus on small business. He and his team grew the Orca Bay Benefits to 300 clients representing over $15,000,000 in annual premium by 2009. Wells Fargo Insurance came courting and in 2009 acquired Orca Bay Benefits during a time when larger brokers were gobbling up smaller brokerage firms. The marriage went well for the first five years but in 2014 it became clear the Wells Fargo Insurance wanted to focus on the larger employers to the detriment of small business. Let’s face it, the smaller profit margins generated by small business weren’t attractive. Wells Fargo was not alone here. All the major brokerage houses shied away from small business.


With renewed energy and a passion to service, Roberts left Wells Fargo Insurance and launched Stillwater Benefits. That was in 2015 and today the Company has grown significantly, added staff and client-facing resources. We mean business. But we’re not trying to take over the world. We simply want to be a key human resource service for select clients – like you!

Our vision is to make our clients feel at ease with their coverages. This includes both the business owner and the employees themselves. We educate, we provide choices and in the end, provide employers and employees with the tools and resources they need to manage their benefits.

We wish to be a best-in-class benefits broker with deep insurance knowledge fueled by a passionate desire to serve. It’s in our DNA. A company devoted to big company benefits for small business – that’s Stillwater Benefits.

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