Boomers Ponder the Selfie Generation

His dream of pitching in the Major Leagues short-circuited by injury, college baseball standout Kevin Waldinger set out to make a name for himself in the corporate world.

The readjustment took Waldinger from the pitcher’s mound at California State Polytechnic University, Pomona to a pair of regional sales posts with Fortune 500 companies until an acquaintance suggested another turn in direction.

After eight years on the corporate ladder, Waldinger was more than willing to listen as the friend proposed that another segment of the business community might be a better fit for his brand of creativity and talent.

“I saw the writing on the wall,” he says. “It’s difficult to sustain a career in the corporate world.” 

The alternative to the Fortune 500 trajectory turned out to be a sales position with CTK North American Insurance Services in Anaheim, a subsidiary of Oklahoma City-based Insurica Insurance Management Network.

Four years after his arrival at the independently owned brokerage, Waldinger has carved out a place as a leading millennial in the industry, helping to dispel an ill-guided notion that this generation is to the insurance field what Kim Kardashian is to articulated thought.

The contributions of Waldinger and other industry up-and-comers born after 1980 (or thereabouts) are making huge strides in persuading their elders—otherwise known as baby boomers—that millennials are equal to the task of reshaping and elevating the industry as it throws itself headlong into the 21st century.

“Millennials are breathing life” into the insurance business, says David Saldon, vice president and director of sales development for Insurica.

An appreciation of what millennials can bring to both sides of the insurance equation—producers and clients alike—couldn’t be occurring at a more opportune time.

“Our industry is fraught with people at the end of their careers,” notes Marty Guastella, vice president of human resources for the Oswald Companies, based in Cleveland.

The supply of millennials willing to replace retirement-age baby boomers in the insurance sector is moreover falling far short of the demand. The generation that came of age in the 1970s—once defined by New Age journalist and novelist Tom Wolfe as “The Me Generation,” because of its infatuation with self-realization and fulfillment in their youth—is having difficulty dealing with today’s “selfie” generation.

Millennials comprise 25% of all business hires nationally, according to Warren Wright, executive vice president of LifeCourse Associates, a northern Virginia consulting firm that specializes in generational demographics. The proportion of millennials on insurance company payrolls? About half the national average: 13%.

The disconnect stems from a 21st-century version of the generation gap, not the least being the perception among the insurance establishment (as well as other segments of the business community) that millennials are gadget-driven, overly entitled, self-absorbed slackers.

Millennials counter with their own biases about a hidebound industry wallowing in a Mad Men-era model of referrals, cold calls and legacy policies.

“It’s a strategy that has been baked into agencies for 25 years,” says Wright, whose organization is credited with coining the term millennials to describe a generation that today spans from ages 11 to 37. “It’s time to break the paradigm.”

Matt Stadler, a 33-year-old senior vice president with MHBT in Fort Worth, Texas, is even more blunt. He says recruiting millennials “is absolutely critical” to the survival of the insurance business.

In Search Of

A highly regarded prototype for recruiting and developing millennial talent is hiding in plain sight in Oklahoma City. That’s where CEO and president Mike Ross and his Insurica team implemented a plan to nurture the next generation of insurance executives. The program, which relies heavily on one-on-one mentoring and periodic status updates with senior executives, was instrumental to the professional development of John Weed.

“From the day I started, I knew what the company expected of me,” says Weed, 29, a former Baylor University quarterback and tight end who joined an Insurica subsidiary in Houston in 2011. “I knew where I should be in three months, six months and 12 months. They didn’t just tell me to sit down, make calls and start making business. It provided confidence that these guys would stand by me all the way through.”

Likewise, at MHBT, Stadler says early guidance from company veterans delivered a powerful message. “Millennials want to feel like they are part of the business, not just a salesman moving on,” he says.

Insurica CEO Ross salutes Saldon, “our millennials guru,” for orchestrating the development of young talent such as Weed and Waldinger. But he confesses that many of the strides made by the firm were born of trial and error.

“I’d like to say we perfected the investment we’ve made,” Ross says. “But some of it was just luck. What we did do, however, was deliver a message that we are committed and invested in them.”

Ross concedes that integrating “fearless” millennials into the mix hasn’t always been “a bed of roses.” His recollection of seeing an inordinate number of ankles bared at important business meetings remains especially vivid. “I’ve had to reinforce the notion,” Ross says, pausing for effect, “that you have to wear socks when you wear a suit.”

Still, the investment has paid off in innumerable ways, perhaps most notably in the companywide appreciation of how the social media that shaped a generation is now defining the industry as a whole. Rather than look askance, Insurica has embraced the technological innovations that have forever altered the way human beings communicate.

In a nod to “millennials [who] like to see their name in print,” Insurica has even launched a network—Ross likens it to a “company Facebook”—that keeps employees abreast of company news, industry trends and the accomplishments of peers.

Robert Smith, the chief operating officer of MHBT, counts the modern tools brought to the workplace among the generation’s greatest accomplishments. 

“Their ability to navigate technology and information—things my generation would take weeks and weeks to do—they can do in a matter of minutes,” Smith says.

Those minutes tend to add up in the age of the smartphone, particularly for the producer living in California with a substantial number of clients residing three time zones away.

“I’ll check my email when I wake up to go to the bathroom at four in the morning,” Waldinger confesses. “It’s kind of sick, but if I see an email from a client on the East Coast, I’ll respond.”

He isn’t alone in staying on the clock long past the traditional office time.

“I don’t shut down at 5 o’clock just because it’s 5 o’clock,” says Stadler. “When I look at the work day, I view it as 18 to 24 hours.”

Smith credits millennials with generating new business through technology. But at the end of the day, he counsels, most deals still come together conventionally.

“The challenge is to convert all the information into action,” he says. “Because you still have to pick up the phone with a prospect on the other side of the line.”

His 24-hour approach to doing business notwithstanding, Stadler takes his boss’s observation one step further. “You don’t ever close a deal without a face-to-face,” he says. “I don’t think that will ever change.”

The Pack

Another millennial trait, collaboration, is causing the business model to evolve.

“They want to work together to make something bigger than themselves,” says Blake Cavignac, the president and founder of YoungPro Elite, whose San Diego consulting firm helps businesses get acclimated to millennials in the workplace.

Ross has watched collaborative efforts surface throughout the Insurica network.

“We’ve seen team-oriented selling and team-oriented support systems and numerous partnerships that have simply developed on their own—not because we told them to do it but because they’ve grown up working with others,” he says.

Teamwork is also key to the mindset Stadler brings to the task—that of a representative selling employee engagement, not insurance.

“It’s a totally different sale than it was 20 years ago,” he says. “You can’t go in and just say, ‘This is the carrier, and this is the price.’ It’s about office culture and employee engagement. [Clients] want to know how to get more out their people, so you need to be proactive.”

Millennials might ultimately prove most influential in the workplace in persuading their peers that insurance is no longer dominated by, as Waldinger puts it, “older white men with briefcases.”

Weed, for one, required only a nudge. The scion of an insurance family—both his father and grandfather were in the business—Weed gravitated to a sales job in the technology field following his graduation from Baylor.

Barely two years later, he followed the path carved out by his dad and grandfather. Competitive by nature, Weed attributes the demands of insurance brokerage for bringing him back to the fold.

“It’s always changing, and you can never know it all,” he says. “It’s a very complex industry, and I’m always looking for a challenge. I always want to know more than the other guy. It helps when I go up against competitors.”

Stadler on occasion finds himself defining to outsiders what it means to be employed by an insurance brokerage.

“Most people don’t know what I do,” he says. “When I tell them I work in insurance, they think of homeowners or auto or that sort of thing. But that’s not what I do.”

Stadler believes it’s critical for millennials to deliver a message to people their age and younger that insurance isn’t a moribund business mired in the past but a “hidden industry that requires you to be highly specialized and develop unique skill sets that, once they are mastered, make you highly valuable.”

Waldinger nonetheless suggests that young professionals interested in pursuing insurance careers launch their careers as he did.

“Go to work in the corporate world, spend three or four years with a Fortune 500 company,” he recommends. “It will benefit you down the road.”

Waldinger has certainly leveraged the formula to his advantage. Ross says Waldinger’s potential as a leader was evident almost immediately. Rather than leapfrog more experienced supervisors and co-workers, Ross says, Waldinger “did it the right way.”

And when the time was right, he approached the CEO directly to outline his objective. “He respected how the process worked and did it in a politically correct way,” Ross says.

At 36, Waldinger finds himself on a career trajectory that former colleagues on the corporate treadmill could only imagine: Insurica in August gave him a major promotion. And he, as the new chief executive of CTK North American Insurance Services, proclaims he is “more than ready for the challenge.”