Insurance Entrepreneur – John Shepherd, CEO,...

Insurance Entrepreneur Spotlight: John Shepherd

In this issue of our interviews with industry leaders, we have the pleasure of sitting down with John Shepherd, Chief Executive of Shepherd Compello Ltd.

Leaving a Large Brokerage to Build Something Better

John’s departure from a big brokerage was not the result of a desire to create an empire, but of a profound exasperation with the level of service that his clients were receiving.

“The business I had built through sweat equity and hard work wasn’t being serviced properly. Clients were on the verge of leaving because of bad account handling, and the country office model back then just wasn’t providing the quality that I wanted,” he says.

In addition to service issues, corporate bureaucracy and internal cost structures were also narrowing profitability and constraining freedom to serve customers in the best manner possible.

A long-term association with EPG Insurance Services in Memphis, which is a large client with expertise in forestry, construction, and trucking, provided John with the confidence to venture out on his own.

“It was about protecting the accounts we’d built and ensuring our clients received the attention they deserved.”

Creating a Business with Flexibility at Its Core

One of the biggest motivators for going independent was the freedom to write the types of business he wanted, without being tied down by rigid corporate policies.

“At a big firm, you’re often forced to pass business over to other departments or decline it outright. Independence gave us the flexibility to say yes when it made sense.”

Even though Shepherd Compello has since developed clear specialisms, the company maintains a willingness to explore new opportunities across different lines, as long as they have the expertise to support it.

Overcoming Compliance and Startup Challenges

Beginning any enterprise is risky — and the insurance industry is no different. When John began Shepherd Compello, he began with three people on staff and forwent 50% of his brokerage in the first year in order to get the business under way.

“Compliance was not as onerous back then, and we had a few big, binding authority accounts to concentrate on instead of a wide-open book of the market. That strategy provided us with a good platform.”

To transit the initial compliance and regulatory challenges, the business had an umbrella-type structure identical to current Appointed Representative (AR) model. John asserts this path remains one of the most sustainable ways for startups in today’s more heavily regulated environment.

“The AR model serves to decrease time and expense. It enables startups to develop a client base and concentrate on service while capitalizing on the compliance assistance of an established canopy.”

Shepherd Compello currently has several ARs and is dedicated to mentoring and their development.

Reducing Barriers for Today’s Startups

The insurance business has come a long way since Shepherd Compello’s infancy. John recognizes that the marketplace is more sophisticated today — but he also senses opportunity.

“We offer our ARs complete back-office support — compliance, claims, finance, marketing, HR — so they don’t have to make such a significant initial investment. That lets them concentrate on relationship-building and business development.”

Since its origin as EPG, followed by its transition to a third-party administrator, and culminating in the launching of Shepherd Compello as a Lloyd’s broker and subsequently White Oak Underwriting, John and his people have developed first-hand experience in broking, underwriting, and administration.

Such a rich heritage positions Shepherd Compello as a springboard for entrepreneurial insurance professionals who want to reach the market sooner and with fewer obstacles.

Insights for Aspiring Insurance Entrepreneurs

As a keen entrepreneur insurance advocate, John’s message to others is one of certainty and expertise:

“Have the courage to believe in your business. If your client base is strong and you can keep those accounts with you, you’re already halfway there.”

He further recommends selecting your niche smartly and matching your values with those of your partner or platform of choice.

“Make sure the class of business you’re pursuing is sustainable. And above all, find a home where your goals and values are understood and supported.”

About Shepherd Compello and White Oak Underwriting Agency

Shepherd Compello is an expert Lloyd’s broker providing customized solutions across many industries. Its sister business, White Oak Underwriting, specializes in niche opportunities within the transport market. Together, they offer an end-to-end platform for underwriting professionals and brokers to develop sustainable, client-focused businesses.

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