Danielle Wyman, VP product and strategy, sets goal roadmaps at Openly

Danielle Wyman describes herself as a generalist who isn’t afraid to ask dumb questions, both of which help her excel as vice president of product and strategy at Openly, the Boston-based homeowners insurance company.

Wyman sets the roadmaps for achieving the goals of Openly’s executive team, such as hitting certain growth or profitability marks. She also prioritizes the various initiatives on tap for reaching those goals, and she works with the company’s technology teams to better understand and build out new technologies needed across the business. 

Knowing about many different aspects of insurance helps her make company-wide prioritization decisions, Wyman says. “What supports me in being a little bit more of a generalist is my curiosity.”

“A lot of people have a career in insurance and it’s down one vertical–they’re a claims person or they’re a sales person. I’ve bounced around a little bit more,” she says. “I was able to be successful because I ask– and I’m sure anyone at Openly would tell you this—I ask a lot of questions and try to understand what we’re doing and what we’re working on and why we’re working on it.”

In spite of her generalist background, when Wyman started in her current position in 2022 her biggest challenge was in an area that she didn’t have a lot of experience in: insurance technology. 

“The lingo–I was a fish out of water,” Wyman says. “I’m in meetings with our CTO and our chief architect and our VP of engineering and they’re going a mile a minute on acronyms I’ve never heard of.” She would quickly learn what a “BE” and an “FE” were, for example—a front-end engineer and back-end engineer—and what the difference was.

“I leaned into that curiosity. I have no problem asking seemingly dumb questions, or questions that feel dumb to me, or interrupting or asking people to stop and explain things to me, having that curiosity paired with not really caring if you need to stop the conversation,” she says. “Relying on my peers who are specialists in this, to help me help them to some extent, has been really helpful.”

Soon after she took the job and analyzed the company’s allocation of its technology teams, she realized that they were misbalanced. They were focused too much on growth initiatives, such as making improvements to the agent portal, and not enough on profit initiatives related to the actual insurance product’s structure and rate changes. The technology allocation needed to change.

“That can be a difficult conversation,” Wyman says. “It’s going to that technology team and saying: We need to make a big shift in the team structure and where people are and what they’re working on.”

The goal is to make sure that the teams’ work is well-aligned with the company’s business priorities, she says. “What are the things that we think are most impactful or most critical to get there? Let’s prioritize them and let’s make sure we have resources allocated to them.” 

Last year, Wyman shifted an initiative to the top of the priority list: Creating an application programming interface (API) to enable real-time Openly insurance quotes via agency internal systems directly, not just the through the Openly portal or aggregators that quote several insurance companies at once. 

The idea hadn’t been a priority, but then several large Openly partners pushed for the new API, Wyman says, plus “we felt it aligned well with our ease-of-use/consumer tech type value proposition.”

“It took a little while to build that initial set up, but now it only takes us a couple days to add on new partners,” she says. “Rinse and repeat.” 

Looking ahead, a key priority will be to evolve the company’s technology to provide great online experiences for agents and customers, similar to the shopping experiences provided by the top online retailers, Wyman says.

“How do we pull some of those great ideas that they have and incorporate them into insurance, and help catapult our experience for agents and customers to where the rest of the non-insurance industry is?” she asks. 

Part of the opportunity for Openly in this area comes from the complexity of that large legacy insurance carriers must deal with as they try to cobble systems together from multiple acquisitions, Wyman says. 

“There’s a lot of stuff that is still very old school out there,” she says. “From a design perspective, we’re thinking about how we compare not just to the competitors, but to the best practices out there.”