Rainmakers of Insurance and Benefits

What does it take to become a standout sales professional in the world of insurance and benefits? Some of the region’s most successful producers reflect on what it takes to lead the pack.




More than 67,000 people in Missouri and Kansas make their living as licensed insurance agents, state officials say, but more than twice that number who are doing business in this region don’t live in either state. Given that there were roughly 1.31 million licensed insurance agents in the U.S. last year, that means this two-state region had roughly twice the agent density of the nation as a whole.

That’s a lot of competition.

“Kansas City is arguably the most competitive city in the country when it comes to the independent middle-market insurance agency business,” says Casey Parisoff, co-founder of the Cornerstone Companies, an insurance brokerage firm. “And that is the way we like it.”

Parisoff has good reason to relish a challenge: He says the Overland Park firm founded in 2009 has experienced growth of more than 300 percent the past three years. With total premium volume of $27.4 million for 2016, Cornerstone has a way to go before challenging hometown heavyweight Lockton Companies, which wrote $4.2 billion in premiums last year.

But while scale may separate the two companies, what unites them is a shared reliance on high-performing sales executives, the Rainmakers of the insurance world. These are the sales pros who drive a significantly disproportionate share of corporate revenues. Although companies in that space tend to zealously guard details of their top performers’ success metrics, there are numerous success factors involved, and Ingram’s sounded out half a dozen firms with questions about the attributes of highly successful agents. 

What they had to say about personal success, team success, and challenges an industry fraught with seismic shifts in its regulatory, demographic, technological and structural fundamentals should be illuminating for anyone who buys insurance, and inspirational to anyone considering a career on that field of battle.

But before going there, a word on insurance and brokerage: While each of the executives interviewed for this report are part of the same broad sector, their companies, products and business models defy ready comparisons or generalizations. While most are pure-play brokers, selling products on behalf of insurance carriers, some focus on property and casualty insurance, others specialize in health and life insurance, and a few deftly play both fields. Others specialize in helping companies craft employee-benefit plans that go well beyond company-paid health insurance.

Underpinning the success of the top performers, though, are some key traits that make them the 21st-century version of the Old West’s gunslingers. First off, they are true students of their industry—they have deep technical understanding of what their products can and can’t do. They are not afraid to hear “no,” and they don’t take that response personally, or as a definitive answer. They are enormously self-reliant, and have the confidence of an NFL cornerback: Yes, you get burned for a long score now and then, but for the most part, you’re a difference-maker for your team. Their orientation uniformly is about team success, not individual achievement. They are innovators who understand they can’t thrive by selling pre-packaged plans, but must craft true solutions specific to each diverse client. They work long hours, and they get up early.

“I love the feeling,” says Parisoff, “of driving by my competitor’s office in the morning and seeing all the lights off.”

Paths to Success

For Jarret Schmidt of Avant Specialty Benefits, an offshoot of brokerage Holmes Murphy & Associates, there is no way to succeed in this sector without being an innovator. “The industry in general is going away from cookie-cutter approaches, with all the pressures on it,” says Schmidt, “With each one of our projects, we’re trying to solve for a unique need a customer has, with either communication, benefit adequacy, or cost savings, so having specific knowledge sets you apart and lets you win.”

Greg Watkins, founder of Watko Benefit Group, says that “what works for us is, fundamentally, we’re driven to help people. That’s what motivates us—pushing the envelope to deliver results for customers.” But technical acumen is huge, too. “I’ve been in the benefit business for 34 years, so I can look at a plan pretty quickly and say there are some things that I can recommend that will make a difference relative to where you are now.”

That’s a key trait for Ryan Wilkerson, as a third-generation owner at Haas & Wilkerson. Quoting an early-career mentor, he said that “if you don’t understand the product intricacies of different coverages, it’s difficult to do a good job helping a client assess risks and helping that business be successful,” he said. “But secondly, insurance is a relationship business. It’s important to have that skill to build relationships, because there are a lot of agents out there—a lot of great agents out there.“

And there are cases where diversity of experience makes a distinction with clients. Before he switched careers to insurance sales 16 years ago, Hays Companies’ Steve Ruben had been the CFO of a trucking company and spent 11 years in public accounting, starting with Deloitte. When it comes to explaining the numbers that can close a deal, that’s a powerful tool. “I’ve been on the buying side of insurance and sat in my clients’ chairs,” Ruben says. “I spent millions on benefits and insurance when I was a CFO, so I can speak to an understanding of the financial aspects of their business and can better evaluate their risk than some others might.”

Working for one of the larger premium-writing firms in the region, CBIZ, Matt Krull says it’s impossible to discount the role of internal support in a producer’s success, especially with the mentoring capabilities available to younger executives. “I didn’t start off in a production role with CBIZ, and frankly, I’m not sure I could have right out of college,” he says. “I was partnered with professionals who took time to make sure I understood the nuances of the business and why we do the things we were and are doing. I began by working on one of our client service teams and quickly realized the importance of providing a high-touch level of service on a consistent basis.“

No one succeeds in sales, in any venue, without embracing the implications of a commission-based income, where you eat what you kill, or you don’t eat. 

“I was raised by a single mother on a commission-based sales income, so I feel like I was always destined to go into the sales arena,” says Parisoff. Starting as a bond-underwriting trainee, he learned the fundamentals of underwriting for contractors, moved to surety and bond underwriting, started his sales career in 2009 and, just four years later, was one of three who partnered to buy their employer out and create Cornerstone.  “Carving out a place at the table for a new business in this industry and, most important, here in this city, has been an exciting and very rewarding process,” he says.

It has also been a demanding one. All of the producers there have a minimum production requirement of $50,000 in new business every year, and “our top producers will put anywhere from $100,000 to $300,000 in new business production alone on the sales board every year.”

Rising to the Challenge

What distinguishes the top producers in this sector, virtually all agree, is the self-confidence to stand out in a world of commission-based income.

“A guy I worked with early in my career would say that it’s not how long you’ve been in the industry that matters, it’s how many calls you’ve made,” said Watkins. “I’ve always thought that was interesting, and I learned that, and applied that. This business is complicated, and it takes time to win new business. There are certain skills that enhance somebody’s ability to make a difference—empathy, persistence, patience, understanding, preparation, and mastering the technical applications of solutions.”

“It’s a pretty compelling industry for a motivated person to get into,” said Wilkerson. “You have to have that ability to build that book of business, and this is different from those where you start at zero every year. With insurance, you are incented to maintain a relationship with a client; if you do that, you can build that book and your income pretty well.”

In general, successful sales execs enjoy competition. What they add to that lust for battle can make all the difference, and there’s no substitute for a track record of success.

“What I’ve learned over the years that has enabled me to make a difference and build on my skills, without a doubt, is knowledge of the business,” said Watkins. “You can have a meeting where there are five or six things you’re working through with a customer that are fraught with potential issues, and without being in the business and going through the challenges and learning, in some situations, the hard way, I think my value as an adviser is significantly enhanced, the fact that I’ve done it as long as I have. Patience develops over time, but doesn’t happen easy; you have to work hard.”

Every producer at Cornerstone, Parisoff says, “started with a book with zero dollars in commission. Sales is not an easy career, and starting a book of business from scratch takes a ton of self-confidence in your ability to succeed.” That means not becoming discouraged after early setbacks. “When you hear, ‘no thanks,’ in this business, you have to get back out there and keep working to find a prospect who needs your services,” he said. “When I started my career I was handed a Builders Association Membership Directory, a cubicle with a phone, and I started at A and ended at Z that week, and repeated the process until I got to where I am today. If you are afraid of rejection. this business is not for you.”

What Lies Ahead

The ability to retain top-producer status is always being challenged by competitors. But there’s a lot more working against one’s continued success in insurance sales than a crowded playing field.

For one, the disproportionate numbers of sales executives over 55, who will soon be cashing out for retirement. Raw numbers of Millennials can supplant the body count, but not the experience.

“It’s a huge issue for our industry,” said Ryan Wilkerson, who, at 41, considers himself an odd duck in insurance management. “When I go to a national conference, generally I’m the youngest person there by a wide margin. That’s changing as I get older, but look around the landscape. As an industry, we’ve not done a good job historically of hiring new younger talent and training them.”

Same goes for his customers, many of whom will be selling their own companies and transitioning out, potentially opening those C-suites to new broker-suitors.

“Whenever there’s a change at the C-level for the consumer, they’re more open to new relationships than the former leader,” Wilkinson said. “That’s definitely something for the sales person to consider when looking for a way to get a foot in the door. We also see some of the same challenges with perpetuation of those companies. I had a client, a Baby Boomer, who sold his business to a big national company, and I lost that account because the insurance was handled by an out-of-country broker.”

Technology, as well, is bound to reshape the sector, he said. “Data analytics is the next frontier,” Wilkerson said. “Insurance is based on the law of large numbers, it’s all about history and data and reviewing things from an actuarial standpoint to come up with a rating that can be profitable.” Agents in coming years, he said, will need to be “more data-analytical to tear apart their client’s exposures and where and why they have claims, and to identify risks before they get out of hand.”

That kind of change won’t be all bad, said Greg Watkins. “I think there are huge opportunities in our field going forward,” he said. “But haven’t there always been? In 1985, they were talking health-care reform. In the 1990s, with the Clintons, same thing. They did it in 2010, and they’re talking about it again. The bottom line is, wherever there is volatility, there is opportunity. And right now, people are looking for new solutions.”

One way to measure success, all say, is by looking at the bottom line. But looking beyond that is important, too. “We certainly monitor the win and loss columns and try to learn what we can from both,” says Krull. “Retention has always been and will continue to be a chief focus on all levels of our organization. At the end of the day, we measure our success by our client’s willingness to recommend our services.“

In recent years, the benefits world has evolved, said Schmidt, moving from relationship-building to technical expertise.  “Now you have to drive results, and you have to provide solutions,” he said. “There will be pressure from legislation and cost challenges, and benefits have taken on a bigger focus within organizations because they are a bigger part of the cost structure. It has become more complicated and you need the resources, tools and abilities to solve problems for your clients.”