<img height="1" width="1" style="display:none" src="https://www.facebook.com/tr?id=1343562685808105&amp;ev=PageView&amp;noscript=1">

CareerAdvisor Blog

The Only Road to Here: Miles Craigwell’s Path to Insurance

Apr 5, 2019 1:49:52 PM / by Magnet Communications Team

It’s human nature to want more, but when it comes to our careers, the “more” can be hard to define. Lateral movements offer a change of environment, but they don’t address the root issue: what we really want is a path forward. Change isn’t enough – it has to be a change for the better.

Miles Craigwell has had a lot of change in his life, and he’s found both success and satisfaction on his path to becoming Vice President of the Executive Benefits Department at M Member Firm Kibble & Prentice Holding Company in Seattle. “I had a particular blueprint in mind that I wanted to follow,” Miles said, “but life threw many curves my way. Instead of resisting, I explored and decided to make these adjustments work in my favor.”

 Miles_Craigwell_Vice President, Executive Benefits USI Insurance

Miles Craigwell
Vice President, Executive Benefits Department 
Kibble & Prentice Holding Company 

From the NFL to Team USA to USI

“After attending Brown University, I had the opportunity to play Safety in the National Football League. After a two-year pursuit, and ultimately floating around free agency, I was forced to contemplate my future and consider my next career step.”

Miles came across a rugby match on television, and despite never having played the game before, he recognized that many of the skills he learned in football would serve him very well in rugby. 

“I asked my agent to get in touch with the USA national rugby coach to see if he’d train me to become an international rugby player. The coach was immediately onboard, and I began intense training with him all summer. In the fall of that same year, I earned a chance to try out for the national team. I was privileged to represent Team USA for six years.”

“While representing Team USA, I was fortunate to travel to ten countries annually for various international rugby tournaments. While on tour I met Chris Prentice, the CEO at USI Insurance Services, who challenged me, while still playing rugby, to build a professional career that would last much longer than my playing years.”

With an Ivy League degree in Business Economics and a global network of connections, Miles wanted to explore this next challenge. “It was my conversation with Chris that drew me to Seattle. I visited and interviewed for a few positions at Kibble & Prentice. The Executive Benefits department, under Bill Walker, was most attractive and aligned well with my experience and academic training. I’ve been a part of the Executive Benefits department for seven years now.”

Looking for your next challenge? Explore the opportunities with M. 


Team Mentality, Individual Success

While new to insurance, Miles had amazing support as he began to learn about insurance. “Kibble & Prentice is much like a sports team in that the employees strive for individual success but are also willing to help and support others. There aren’t many sharp elbowed employees at our brokerage, and much of my success can be credited to the mentors I’ve had along the way.”

Given his experience in professional sports, Miles is well aware of how an injury or disability can severely impact or disrupt one’s ability to continue playing.

“Competitive athletics requires optimal performance that sometimes pushes the body beyond its comfort zone. The nature of rugby can be violent and aggressive, and for some, comes at a cost. Many athletes get injured during their careers. Those who are lucky to walk away without injury are fortunate and rare. Educating executives, athletes, and entertainers about the risks of injury or disability often comes through the personal experiences I’ve had, or experiences I’ve seen friends and colleagues go through. For that reason, it’s been a natural progression for me to be an advocate for these lines of coverage.”

Despite rugby players being fierce competitors, Miles developed a large network of friends and teammates through the camaraderie of the sport.  

“Rugby is unique. After the match, you enjoy a few ‘cleansing ales’ with the opposing team. There’s a lot of banter and laughter, and long-lasting relationships are formed at these after-match socials. Many of the rugby players I’ve met over the years have organically become clients over time. It’s fun to see these two worlds come together.”

Miles credits his openness to embracing the unknown to the success he’s had in the insurance industry. “I came to Seattle not knowing what was out there or if I’d make it in this industry. I’m in my current position at USI Insurance Services because I pursued the unknown. For anyone looking at the insurance industry as a new career, I would tell them to explore their options and see for themselves what this industry has to offer. I encourage anyone considering the Magnet program to give it try. Given all of M Financial’s resources and support, I am confident you can be successful, and have a lot of fun along the way.”

There are many paths to success in the insurance industry. Magnet can help you get where you want to go more quickly.  Learn more about the Magnet program.



Topics: Becoming a Financial Advisor