Table of Contents 


Marketing Agency of the Month

Winning the ties

Competitive fire keeps Shepherd Insurance moving forward

By Dennis H. Pillsbury

“Success is peace of mind which is a direct result of self-satisfaction in knowing you did your best to become the best that you are capable of becoming.”

—Former UCLA Basketball Coach John Wooden

This was the founding principle that David Shepherd, CEO of Indianapolis-area Shepherd Insurance and Financial Services, utilized in establishing his independent insurance agency in 1977. As Indiana’s 1970 Mr. Basketball and a former academic All-American at the University of Mississippi, Dave understood the formula for success early on.

His high school basketball coach, Bill Shepherd, who also happened to be his father, instilled this formula of success within Dave and encouraged him to enter the insurance industry instead of pursuing a career in coaching. The core values of having a winning attitude, an intense competitive spirit, outworking the competition, and refusing to lose is what affords Shepherd the ongoing opportunity to win “ties.”

Recalling the early struggles of building an agency from scratch, Dave remembers, “I basically went door to door, and Dad went along with me on most of my calls. Fortunately, I was pretty well known in my hometown of Carmel, Indiana, thanks to my basketball career. That didn’t mean that people would just buy insurance from me, but it did mean that they usually would listen to what I had to say.”

“It was all about developing relationships; and still is. But, my initial relationships only afforded me the opportunity to compete,” Dave explains. “It was like a close game of basketball. When the score is tied, the team that works the hardest and is persistent on defense will win.

“I kept winning the ties by going that extra mile for each client,” Dave says. “Eventually, customers were asking me for help with all of their insurance coverages, so I went out and tried to find an insurance company that would give me a contract.” In 1981, Erie Insurance afforded Dave the opportunity to step up to the next level.

In 1984, his friend and current CFO, Jeff “Q-Man” Kweder, joined the agency. Jeff brought with him the same core beliefs of being extremely competitive and highly motivated. His financial vision and marketing perspectives made an immediate impact at Shepherd Insurance. A former college golfer, Jeff started a trend at Shepherd Insurance that has been carried forward for more than 20 years—hiring former elite athletes.

Everyone on the current sales team of 20 producers has a successful background in athletics. The sales staff’s background ranges from a former NFL football player, Big 10 basketball players and coaches, college and minor league baseball players, professional runners and triathletes as well as former college tennis players and golfers. They share common attributes such as self-discipline, the ability to multi-task, the competitive drive to succeed, the ability to overcome adversity and a commitment to excellence.

Even with a good foundation of relationships, the agency’s early years were challenging. They operated out of a garage converted into an office. “Our office was so small that we never invited clients to come see us,” Jeff recalls. “We’d always say: ‘You don’t need to go out of your way. We’ll come to you.’ We used a soft sell approach where we’d ask people to give us a chance to show them how hard we would work on their behalf, and we were persistent. Neither Dave nor I are good at taking ‘no’ for an answer.” Despite those challenges, Dave and Jeff were selling nearly 200 new policies a month.

“We had a lot of friends and developed more,” says Dave. “Soon, our personal lines clients were asking for help with their business insurance needs. We were only too happy to oblige and began writing small BOPs for personal lines and life customers.”

Dave continues, “We always wanted to write as many policies for our clients as possible. They were much less likely to leave the agency if we had three policies instead of just one. It helped us develop strong relationships with each client that couldn’t be broken. It also increased the number of touches with each client. We want our customers to remember us and to call whenever they have a question or there’s been a change in their insurance needs. And they do.

“That was our way of doing business when we started and it continues today,” Dave says. It’s certainly one of the reasons that Shepherd Insurance boasts a customer retention ratio of 95%.

$7 million and growing

Today, Shepherd Insurance and Financial Services continues to operate in Carmel as well as in Evansville, Indiana. “We built our headquarters in 1996,” Dave says, “when the agency started to grow, but we had no real assets except our employees and our customers. Our agency needed to establish a visible presence in the community, so we managed to convince a local bank and the SBA to take a chance on our company. Many colleagues, business acquaintances and friends thought the plan was a bad idea, but it was just the opposite. The agency gained instant credibility, and started growing at a rapid rate.”

Since 2003, the agency has added more than a million dollars in revenue each year. Revenues will exceed $7 million this year, and nearly all of that is organic growth.

The Shepherd Group acquired an agency in Evansville in 2003 that had about $400,000 in revenue and five employees. This year, the Evansville branch will exceed $1 million in revenues. The agency also recently purchased a building there to handle the growth. The Evansville branch, now run by Chief Marketing Officer Quinn Shepherd, has 20 employees and its headquarters in Carmel employs 50 people.

Jeff adds, “Our revenue balance of 30% commercial lines, 30% employee benefits, 30% personal lines and 10% from 401(k) and investments helps cushion us from the soft markets in one area of the business. We haven’t forgotten the people and the type of business that got us started. We continue to focus efforts in all four revenue-producing areas including personal lines, where our foundation was built.”

Niche markets

Like many successful agencies, Shepherd Insurance has developed niche markets where their unique expertise, insurance carrier relationships and value-added services differentiate them from the competition. Many of these niches were established by taking advantage of being at the right place at the right time. One of the agency’s most significant market niches, the franchise truck dealership industry, is a prime example.

Dave recalls, “In 1990 our agency’s office was located next to the regional Mack Truck franchise sales office. A friend from this office referred a potential client who was purchasing the local Mack dealership. The dealership was struggling at the time. The new owner, Shelby Howard, had a similar business style to ours, and we clicked immediately. Although we initially were working only on his garage insurance, this opportunity allowed us to attract this fledgling dealership’s group benefits and 401(k).” Today this dealership has become one of the most successful Mack/Volvo franchises in the country with more than 400 employees in eight locations.

As a result of developing a business and personal relationship with this one account, Shepherd Insurance has been able to parlay the franchise truck niche into an established program insuring more than 50 dealers for casualty, employee benefits and 401(k) plans. “More than 15 years later our original customer, Shelby Howard, is still one of our best salesmen,” Dave says. “He constantly recommends us to colleagues and business associates.”

In July 2006, the Auto Dealers Association of Indiana named Shepherd Insurance the exclusive agent for their association-owned insurance company. In just over one year, Shepherd has written casualty insurance coverages for 60 dealers, with a potential to reach a total of over 600 dealers in the association. Other niches that Shepherd has developed with insurance carrier partners include programs for commercial real estate developers/owners, physician practices, electrical contractors and golf/country clubs.

Administrative talent

Like many agencies, Shepherd evolved from a small, sales organization to a business that needed to take care of its employees, keep pace with automation and provide quality service to a growing number of clients. No matter how hard Dave and Jeff were willing to work, there were just not enough hours in the day to continue to provide exceptional service to a growing clientele. Fortunately, Dave’s oldest daughter, Kelly Shepherd Kakone, provided a perfect complement to Dave and Jeff, with her organizational skills and vision for the agency’s future in the next generation.

Kelly has been with the firm for 13 years. In that time she has worked in a variety of roles, including producer, and is the current president of Shepherd Insurance. “As we grew we needed to work smarter,” Kelly says. “Today that means using automation to provide services where it makes sense. We continually reinvest in technology so that we can stay ahead of the curve.”

The agency now employs a full-time IT professional with the sole purpose of making sure the agency’s automation systems run efficiently and to utilize technology to better serve clients. In recent years Shepherd has invested in customer value-added tools including ZyWave, MyWave, Mod Master and an online employee benefits enrollment service.

The agency has an underwriter on staff who understands what their insurance carriers want and can make certain that their clients and carriers mesh. Kelly says, “We’re not afraid to have our clients and the company underwriters meet. In fact, we encourage it. The more the underwriters know about the client, the better the chance that they will treat that business favorably. We’ve worked very hard with our clients to make them attractive risks and we want the underwriters to see that first hand.”

The agency offers a loss control program, partnering with Safe Metrics to help clients mitigate or eliminate potential losses. “Our insurance companies see what we are doing when they visit with our clients and also when they look at the good loss histories we produce for them year after year,” Kelly says. “They know that we don’t shotgun business.”


“Probably my most important job is listening,” Kelly comments. “We are fortunate to have amazing people working with us. We are competitive in the benefits we offer employees, along with offering excellent salary and commission structures.”

The agency has regular meetings with the staff to update them and to hear employee concerns. It also has an annual off-site corporate retreat that involves representatives from every department. Everything is discussed, and management solicits ideas from everyone.

Dave says, “We let the staff know that nothing is off limits, and based on some of what is said, the employees really believe that. They present ideas that will improve service to clients and the work environment. I want to hear everything.” After the last corporate retreat, within a few weeks 75% of the ideas presented on how to improve the company were implemented. The agency wants to communicate to its employees that their ideas matter.

One of the first ideas implemented was establishing platinum accounts and developing a unique service model committed to these customers, which includes the producing agent, an account manager and a dedicated services representative.

The importance of listening also applies to Shepard’s relationships with clients. “We want to understand our clients’ style of doing business just as much as they understand ours. If we don’t listen to our clients, it won’t matter how well we listen to our employees, because there will be no clients to service,” says Kelly. The agency encourages clients to provide feedback during meetings and by visiting their Web site and taking a client survey.

The people

The agency is poised for continued growth. “We’ve hired a number of young professionals who are just starting out in the business,” Jeff points out. The agency has six producers on salary who are learning the business and developing new relationships. These producers, all former athletes, are provided sales training by senior agents within the organization.

The team approach is engrained early on. The producers are provided a salary for up to three years as they are acquiring product knowledge and developing a customer base. Part of their training consists of quarterly all-day sessions with an executive sales consultant, Jeff Jenkins, from Marsh Berry & Company. New producers travel with senior agents to visit with current and potential clients. Jeff says, “We want them to understand how important developing a relationship with a client is and what’s involved in truly servicing an account.

“We have worked with Ball State University and Indiana State University to find young people who are interested in the business,” Quinn adds. “Often we get recommendations from young people who work for us and know that a classmate might be a perfect fit. This is what will keep our agency growing into the future. The enthusiasm and energy these young people bring to the agency is contagious.”

Dave comments, “We can train producers on the insurance side of the business, but you can’t train someone to be a winner. We hire winners, people with a commitment to excellence.”

The agency has had the opportunity to be involved with insurance industry organizations that have helped the company grow and improved their skill sets. Dave says, “We are grateful to have been befriended and mentored by some of the most respected and successful insurance professionals in the industry such as Scott Addis of The Addis Group. We also feel fortunate and proud to be part of Marsh Berry’s APPEX Agent Group.”

Giving back

Shepherd Insurance is involved in giving back to the communities in which it operates and to the industry. “We’re sensitive to being human beings,” Dave says. “That really is our most important job. Our company supports a variety of social programs like Habitat for Humanity, The 50 Club (supporting local police and firefighters), the YMCA in Evansville and the local school communities with sponsorships like the Hamilton County Holiday Basketball Tournament.

“We also encourage our staff to get involved in community organizations. We pay their dues and give them time off if they need to attend meetings or help out with a community project. And we lead by example,” Dave says. Kelly serves on three boards: the Young Presidents Organization, Goodwill, and the regional “Big I” Insurance board. Dave serves on the board of Camouflage for Kids, a charity dedicated to families whose loved ones are serving our country in the Middle East. Dave; Quinn and Jeff are all involved with a number of community organizations, including the Chamber of Commerce and Rotary.

“We also recognize how important it is for our people to understand and support the industry we serve,” Dave adds. “We pay for continuing education for our people who are seeking advanced insurance designations and encourage everyone to keep abreast on what is changing in our industry.”

Part of Shepherd’s strategy is to invest in the future and actively seek out opportunities to acquire other agencies. The agency knows that not every investment will pay immediate dividends, but believes it is essential to invest in its people, in the community, in automation and in education for the long-term success of the organization.

“We’re a family of 70 employees and growing,” Dave says. “We have made it clear that we are not for sale. This is our agency and it’s going to stay that way. Our people really appreciate that and see that we’ve invested in making certain we can stay independent.” The lineup of the Shepherd management team shows the agency’s commitment to building a legacy: The chief marketing officer is in his 20s, the president is in her 30s, the CFO is in his 40s and the CEO is in his 50s.

Shepherd Insurance represents the best of the independent agency system—involvement in the community, the industry and excellent value-added service to its clients. Rough Notes is proud to recognize this agency as our Marketing Agency of the Month. *

Click on image for enlargement 

David P. Shepherd is CEO of Shepherd Insurance and Financial Services in Carmel, Indiana.


The Shepherd Insurance management team includes (from left): Dave Shepherd, CEO; Jeff Kweder, Chief Financial Officer; Kelly Shepherd Kakone, President; and Quinn Shepherd, Chief Marketing Officer.


Quinn Shepherd (second from right) meets with senior insurance and benefits advisors from the agency’s Evansville branch to discuss renovation plans for its new Evansville office.


In 1990, Shepherd Insurance began providing insurance for a local Mack truck dealership, from which the agency established a successful franchise truck dealers program. With Dave Shepherd (right) is Shelby Howard, owner of that first Mack truck dealership.


The youth at Shepherd Insurance represent the agency’s strong commitment to perpetuation.


Shepherd’s producers have backgrounds in competitive sports, fueling the drive and team atmosphere that exists at the agency.


Carmel Mayor Jim Brainard (second from right) recognizes the Shepherd agency’s involvement in the community.