When it comes to leading, Ben Jennings loves winning as a team.

That means tapping into the best of each team member for the betterment of the whole. But Jennings doesn’t sugarcoat.

He knows it’s challenging to do that at an insurance technology company, where finding a combination of tech folks who embrace the complexities of insurance and insurance pros who embrace the opportunity technology holds is “surprisingly difficult,” Jennings said.

“You end up with insurance people that push back and feel like humans have to do the work … and then you end up with technology people that don’t truly understand the nuance and complexity of underwriting risk, managing data, claims history and all of this stuff,” he continued. “And so, you have this mishmash.”

He underestimated the challenge when he entered the InsurTech industry. Today, he believes his team has got it right.

“At Embroker, we have spent a lot of time and energy on our people and culture,” Jennings said. “We went through an evolution, have matured as a business, and have since continually invested in the marriage of insurance and technological expertise.”

Jennings grew up in Northern California before cell phones, email and the Internet had gained mainstream popularity. He jumped into technology after graduating from Santa Clara University and worked stints at several early advanced networking and infrastructure companies. It was in these roles that he worked alongside numerous industry luminaries who got him hooked.

“That pace, and that sense of disruption and creation, was something I was thrilled to start my career in,” Jennings said. “And that really took me through the better part of 30-plus years.”

He worked in leadership roles at ServiceSource, a revenue-as-a-service platform designed to help companies efficiently and effectively find, convert, grow and retain their B2B customer relationships, for 16 years. (That company was acquired by Concentrix in 2022). Jennings helped the company grow from 35 employees to more than 4,000 with global offices.

After what Jennings described as “a really incredible run” at ServiceSource, he decided he wanted to make a change. Specifically, he wanted to do something disruptive. He wanted to find a place where technology “hadn’t been so pervasively adopted. It hadn’t been saturated with good ideas already,” he recalled.

Research pointed him to commercial insurance. Jennings met Matt Miller, the founder and former CEO of Embroker, and he learned about the company’s objectives. Jennings was on board.

“It was a very straightforward value proposition that lent [itself] so incredibly well to melding traditional insurance practice with technology that I was in,” Jennings said. “And that was almost six years ago now.”

Embroker strives to be a single destination for businesses of all sizes to apply for and purchase insurance coverage that is tailored to their specific business needs. The platform specializes in working with venture-backed technology companies, private companies, law firms, and real estate consulting and accounting businesses.

Put simply, Jennings said Embroker aims to make it easy for businesses to efficiently get the coverage they need at the right price.

Instead of shopping multiple brokers for coverages and filling out multiple complex applications for policy types, Embroker uses artificial intelligence and advanced data to streamline the process to a single online application. The company’s aim is to offer a digital experience both for business owners who know what they need and for those who need guidance. In either scenario, users enjoy a fully curated process that guides them through insuring their business based on their specific needs, Jennings said in follow-up communication.

“Effectively, think of it as embedding the mind of a broker into that technology,” Jennings said, “and embedding the work of a broker and a traditional marketing team, but in an automated way, so that you have this digital experience that is much quicker and friction-free. Then, we’re providing expert guidance along the way to answer any customer inquiry.”

Customers can go through the entire process — from application to bind — without speaking to a human. Embroker’s in-house brokerage arm is available, too, to support policy buyers and help with anomalies and issues, Jennings said.

When he entered the insurance technology world, Jennings said he brought with him a speed bias. He needed to acclimate to the level of patience necessary to thrive in the heavily regulated and slow-changing industry. Today, however, he sees Embroker as a hyper-efficient company as it pushes ahead.

“Our most strategic asset is our incredibly talented team,” Jennings said. “Continually fostering a culture of collaboration and learning has allowed these two critical worlds to come together, allowing us to deliver a truly meaningful insurance experience for our customers.”

He hopes his employees see him as fair, honest and transparent.

“You cannot make everybody happy all the time,” he said. “In my career, I would prefer people to know that they know exactly where they stand with me. They feel like I am never unfair, or I didn’t inform them, or we didn’t communicate properly. I try to operate with as low an ego as possible and as humbly as possible.”