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Pogo Helps Self-Employed People Get Insurance Without Getting Headaches

Founded by married couple Hannah and Jade Sullivan, Pogo wants to make finding insurance easier for startups, freelancers, and small business owners around Richmond.

Sarah Honosky | February 14, 2018

A new Richmond startup aims to make insurance easier. Pogo, co-founded by married couple Hannah and Jade Sullivan, employs simple, streamlined aesthetics and easy accessibility to make a straight-laced vocation look a little less conventional.

Pogo is an online business insurance agency for the self-employed. It works to cut through the clunky jargon and complexities of the insurance business, and simplify the experience. “People don’t really know where to start, or what insurance companies can help them, so they spend a lot of time and energy trying to figure it out themselves… So we’re sort of bridging that gap,” said Hannah Sullivan. “You can get insurance from your couch.”

With numbers of self-employed Americans on the rise – some studies project that by 2020 more than 40% of the American workforce will be independent workers — easy and accessible insurance is a necessity. The increasing share of the workforce operating as independent contractors are ineligible for workplace benefits, and must pay for insurance out of pocket. This process is not only complex, but takes time away from the work that matters to them. Without something like Pogo, they often don’t have insurance at all.

Hannah and Jade are familiar with the frustrations of insurance, and are fully committed to making things easier for the freelancers, entrepreneurs, startups, and small business owners who populate Richmond.

“We also have friends who have worked with two or three different insurance agents because they can’t get all of the coverage they need in one place,” said Jade. “But we can provide everything you need, kind of like a one-stop-shop.  You just fill out a simple form and we compare over 30 top insurance companies, for free.”

It’s no secret that insurance is a male dominated field. According to a Credit Suisse report, just 1% of insurance firms have a female CEO, and only 12% of women in the industry are in top management positions. But Pogo is headed by two married, gay women, neither of which fit the gray-suited insurance stereotype.

“If you compare us to the people in our industry, we already look different because we come from a creative background,” said Hannah. “Jade [had] half her head shaved and I had a faux-hawk when we first started working in insurance in 2015… We were already different. We have nothing to hide, and we’ve never hid the fact that we were together. We just didn’t make it a thing, and no one else did, either.”

Jade and Hannah Sullivan with Hannah’s dad, Steve Lane. Photo via Twitter.

When Hannah was stuffing envelopes at her dad’s insurance company in high school, she had no intention of ever coming back to the field. “I was a funky chick with colorful cowboy boots, and knew I wanted to work in the design world, not the insurance world.” But when her father, Steve Love, an industry veteran with more than thirty years of experience, offered them an opportunity to be a part of his new backend insurance program, Hannah and Jade left the New York creative scene to join the project.

“At first it seemed like we were out of our element, because insurance is so bulky and formal,” said Hannah. “But as we broke down the process, we realized we could make the experience of finding insurance better through design.”

As graduates of the VCU Brandcenter, which is part-creative studio, part-business school master’s program, they were already predisposed to look at the field differently. Hannah is experienced in graphic and web design, and Jade does UX/UI design, so creating a user-friendly interface was a primary focus. “I think that who we are in general kind of gives us an advantage,” said Jade. “Being designers/creatives kind of gives us an edge to look at things from a different perspective.”

Their experiences at the Brandcenter didn’t just equip them with the design abilities they needed to create Pogo, it was also the place where they met. Jade asked Hannah if they could work together on a project, and after that, they never stopped creating. They began a side project that involved coding, design, and animation, pushing themselves through projects outside of their comfort zone.

“I think that’s when we realized how much we love figuring things out together. It was also the moment we realized we could do anything together if we tried,” said Jade. “Once we realized we could apply new thinking to anything, we started inventing random things all the time for fun, but we never settled on anything because honestly it was all kind of pointless. It wasn’t until Steve proposed we apply ourselves the insurance industry that we felt like we could really make an impact.”

Hannah and Jade have high hopes for Pogo’s future. In a field that provides more headaches than help, they are looking to change the game.

“Pogo has what it takes to be a mega resource for the people who are changing the workforce, and the economy,” said Hannah. “We’re here to protect people, to ensure their success, and to help self-employed people all over the country kick ass.”