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Flagship Insurance Services

A One-Stop Shop for Tailored Employee Benefits and Risk Insurance for Business

Nick Kuchenbecker, Owner and VP of Sales and Jennifer Sherman Stratton, Owner and CEO, Flagship Insurance ServicesNick Kuchenbecker, Owner and VP of Sales and Jennifer Sherman Stratton, Owner and CEO
Flagship Insurance Services is a full-service Twin Cities insurance agency whose customer-first mindset, industry knowledge, and adoption of technology has resulted in explosive growth and, more importantly, a satisfied client base. Led by Jennifer Sherman Stratton, owner and CEO, and Nick Kuchenbecker, owner and VP of Sales, Flagship prides itself on its white-glove level of service. “This doesn’t mean the same thing for every client,” says Jennifer. “Over the past four years, we’ve researched, tested, and adopted technology we feel will help us serve our clients better. More importantly, many of our tools go beyond insurance to help our clients serve themselves. This is what allowed us to maintain our organic growth even during the COVID disruption.” Jennifer’s comment may be a bit modest as the company’s revenue has doubled in that same four-year span.

As companies tackle the challenges of a dynamic work environment and increasingly remote workforce, they are looking for digital solutions to keep their back-office services running smoothly. “We feel like this is our strong suit,” mentions Kuchenbecker. “While we’re fine with, and excel at serving our clients the old-fashioned way, the demand for digital adoption and self-service for employees is real. It’s growing and we are already there.”

Flagship partners with its clients to help them build their technological capabilities. “When COVID hit, the vast majority of our clients had already transitioned to our automated and cloud-based tools and were not impacted as heavily,” states Jennifer. “And, we know these tools very well, because we use them with our own staff at Flagship. We walk the talk so when we partner with our clients’ HR organizations to help them with implementation and ongoing management, it’s easy to speak to the benefits.”

Kuchenbecker was quick to point out what some of those benefits are: “Most of our clients are very busy in the fourth quarter. We create custom tools and employee communication to manage the process from start to finish for our clients. These tools also facilitate our clients’ employees to self-service their open enrolment and share the information with the decision makers of the household. The HR folks really like that,” he adds.


Over the past four years, we’ve researched, tested, and adopted technology we feel will help us serve our clients better. More importantly, many of our tools go beyond insurance to help our clients serve themselves

And, Flagship doesn’t use third-party vendors to manage the platforms they advocate. This saves their clients money.

“We always want to be good stewards of our clients’ dollars. It was a big learning curve to keep this expertise in-house but it was worth it,” asserts Jennifer. The platforms they offer enable clients to automate other back-office tasks as well, such as compliance integration, salary benchmarking, performance reviews, and many others.

Kuchenbecker adds that the technology is not as valuable without the expertise behind it. He specifically calls out Jennifer’s experience, “Jennifer is very highly respected among her peers.” It was this cache that landed Jennifer a seat on the Minnesota Health Care Reform Task Force to advise on health care reform. “She’s our leader. Our staff tries to replicate the high standard she sets. This high standard is why I wanted to join Flagship,” informs Kuchenbecker. In fact, Kuchenbecker’s twenty-plus years of experience in the insurance and compliance services industries has complimented Jennifer’s skillset well. “Kuchenbecker is a visionary. He’s an idea generating machine,” affirms Jennifer. “I just need more time to implement them all!”

Flagship is a full-service insurance agency offering life, health, automobile, and travel insurances, employee benefits, worker’s compensation, retirement, and investments, and more—all under one roof. Actually, two roofs now that the company has recently purchased retail space in Southwest Minneapolis and remodeled it into a collaborative workspace complete with eight workstations, three conference rooms, and a 16-foot concrete collaboration table. It also tips a provincial hat to a few local musicians with two piercing paintings of Prince created by a local artist. “Since insurance brokers and many of our clients are opting for a workstation-like atmosphere with all the visual tools at their disposal to deliver ornate client presentations, we came up with this shared space concept,” mentions Kuchenbecker. This outside-the-box approach to their expansion garnered an article in “Insurance Minnesota.”

Flagship’s vision for the future is bright. “To continue to thrive in this industry, we need to remain focused on providing value for our clients,” informs Kuchenbecker. “Constant researching, innovating and networking is essential to our business,” concludes Jennifer. “It’s where we discover ways to continually improve our services.”

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Top 10 Employee Benefits Services Companies - 2021

Flagship Insurance Services

Company
Flagship Insurance Services

Management
Nick Kuchenbecker, Owner and VP of Sales and Jennifer Sherman Stratton, Owner and CEO

Description
Flagship is a full-service insurance agency, offering life, health, automobile and travel insurances, employee benefits, worker’s compensation, retirement, and investments, and more—all under one roof. The company’s customer-first mindset, industry knowledge, and adoption of technology has resulted in explosive growth and, more importantly, a satisfied client base. The platforms they offer enable their clients to automate other back-office tasks as well, such as: compliance integration, salary benchmarking, performance reviews, and many other tasks. Flagship doesn’t use third-party vendors to manage the platforms they advocate—which saves their client’s money