Agency Profile: Millennial Moxie

APProsper Insurance

Virginia Beach, Virginia
Founded: 2011
Employees: 50

After a stint owning an Allstate agency, Prosper Insurance President Drew Monroe went out on his own, intending to focus on commercial lines. “But then we started thinking about scaling,” he says.

Commercial lines producers were expensive and took lots of time to train. “We felt like most local agencies that were soph­isticated focused on commercial lines,” he says. “The agencies that were not as sophisticated focused on personal lines. So, we stopped writing commercial and focused on personal—and it served us well.”

The agency has grown from four to 50 employees without acquisitions. But perhaps the most telling statistic of this growth-focused agency is the median age of its employees: 28. “I’m 36, and there are only two employees here older than I am,” Monroe says. “It’s a stark contrast to the average independent agency.”

Prosper resonates with both its millennial employees and customers through the agency’s core value of giving back. Each quarter, employees participate in a volunteering day for local organizations. And for every policy the agency writes, a tree is planted on behalf of the client. “It’s a way we can consistently give back,” Monroe says.


Our agency’s culture separates us. We have a young, energetic sales team that likes to control their own paychecks.

We like to hire from referrals from friends and family of current employees. Four out of five hires have no insurance or sales background. They go through an intensive insurance 101 training program and get their license before they come on board. The training department goes above and beyond to make sure employees are supported—no one is ever in the weeds alone.

I’ve not had to make one cold call since I’ve been here. We do all our own inside sales and marketing through direct referral partners—loan officers, financial advisers, real estate agents. We call them regularly thanking them for a sale or asking what we can do differently.


The secret to our success is a commitment to constantly tweaking the way we do business. Every two weeks, our management team meets to discuss how we can imp­rove our value proposition. We all leave that meeting saying, “In the next two weeks, I will have X done”—and then we hold each other accountable.

Carrier reps often come into our office and say, “Wow, this feels different than other agencies.” From a culture standpoint, we are the yin and the yang. On one hand, you feel this casual atmosphere—people are casually dressed and younger, and there is funny stuff on the walls. On the other hand, we have high performance standards—our goals are on the wall, too, and you can see who is at the top of the leaderboard.

If you define “professional” by the way people dress, we’re not. But if you define it as fast, efficient and reliable service, we’re the most professional agency out there.


Originally, our producers serviced their own accounts. Then the agency outsourced service. And then we realized we could do it better ourselves—and the results speak for themselves with our agency’s high net promoter score.

Even though we have distinct sales and service teams and we are on different floors in the office, it’s a false separation. The teams mix and mingle, and we really try to understand each other’s point of view.

We have great employees who are obsessed with our clients. If a client is having a bad experience, we brainstorm as a team to find creative solutions. We really educate our service team—we can do more than just switch a car on a policy. Our team is well-equipped to explain the policy and make sure our customers feel comfortable. We are guardians for our clients.

Photo by Steve Budman