Jerry's Stephanie Ubaldini builds enthusiasm for insurance: WIL NEXT 2022

Stephanie Ubaldini has been a key part of a small, but mighty, insurance community forming around Buffalo, N.Y. Beginning her career in Geico’s burgeoning regional office, she later moved to the insurtech Jerry, a digital agency with operations in the area. At both stops, she’s been charged with onboarding associates to growing staffs, and getting them enthusiastic about insurance. But her original career plan was somewhat different.

“I was convinced I was going to be a news anchor when I graduated from school. I did get a job immediately after graduation at a local news station. I worked for about nine months as an assignment editor in the newsroom,” she says. 

But after some layoffs at the station, “I looked at Geico’s website and they had a ton of jobs, including a sales job. I had always been a pretty competitive person, so I thought I would do well in sales. Lucky for me, that turned out to be true,” she continues.

After demonstrating a propensity for sales at Geico, she joined the carrier’s leadership program and moved onto the training path she’s continued down since. 

“Once I got that first dose of, ‘I can make an impact on somebody else’s career and performance while simultaneously positively impacting the business,’ I was hooked,” she says.

Ubaldini was recruited by Josh Damico, Jerry’s VP of insurance operations and, like her, a Geico veteran, to join Jerry. She says that working for the digital agency startup after so much time with a single carrier was different, but rewarding. Over the course of her time at Jerry, the company’s business has doubled, as Ubaldini’s agent onboarding has kept up with increased demand for its services. She now manages more than 130 people across five different units as director of sales and service.

“Your mindset changes from caring about one specific company to caring about the customer and what company fits the customer the best. Ultimately that is what’s going to make Jerry successful,” she says. “We are a digital agency, we want to help as many people as possible find the best product that fits their needs.”

Joining Jerry during the tail end of the COVID-19 pandemic, as the company was transitioning from a fully on-site operation to one with more remote options, required new thinking on a different front as well. Not only was she working for a different kind of company, but the recruitment, onboarding and training processes were re-architected to be virtual. With a recruitment pool as large as the U.S. and with so much demand for more agents, Ubaldini built a program that could serve applicants next door or as far away as the west coast.

“Insurance is complicated and overwhelming for people who are just getting into it. There’s a lot of information, but the world that we live in is not built for lectures and long reading anymore,” she explains. You need to figure out ways to engage people, building in a lot of practice and simulation. You have to check for understanding to make sure consistently that not only are people engaged, but they’re retaining the most important information.”

In recruitment and training, however, Ubaldini draws on her own path to insurance from a totally different industry to make sure she sets people up for success. 

“No kid dreams about being an insurance agent when they grow up. But what a lot of people don’t understand is just how important insurance is to people’s livelihood,” she says. “This may not be a sexy industry, but if you do this job really well you could be covering and taking care of somebody when they need it most, which is incredibly rewarding.”