Sarah Tomaro: WIL Next 2024
Among her qualities that predict “strong C-suite potential,” Sarah Tomaro, director, operations analysis and reporting at Openly, doesn’t shy away from offering her objective appraisal of colleague proposals, even when the truth hurts, according to her manager.
“Sarah is comfortable recommending inaction or de-prioritization when appropriate, even if it is not what an operational stakeholder wants to hear,” says Rob Higgins, chief product and strategy officer for the Boston-based homeowner insurance company, which launched in 2017.
As the leader of an analytics team that assesses potential opportunities and ongoing initiatives, Tomaro says, she tries to show that her no-go assessments are well-researched and based on comparisons to other potential projects. “Grounding it in facts helps make that conversation less awkward.”
“Sometimes people have really cool or interesting ideas that might be fun to look into, but they’re not necessarily going to add a lot of incremental value,” she says. “We have limited resources and time, and we need to focus on the things that have the biggest return for us.”
When she joined Openly in 2021, her initial challenge was to build her new team and educate leaders within the company about what that team could do for them. She also had to learn from those leaders about their work and their priorities, and then identify opportunities for growing their businesses or finding efficiencies.
“I had to really work to establish those relationships, get buy-in from the leaders and get them more and more comfortable with throwing questions to us and partnering with them in terms of delivering insights,” Tomaro says. She knew getting incremental buy-in would pave the way for more projects and bigger projects later on.
Once Tomaro and her team started fielding more and more requests, her challenge shifted to keeping up with all of the potential projects and prioritizing them. She would hold scoping sessions with company leaders so she could understand the questions they wanted to address and make sure they tied into a larger objective for the company. Projects that connected to multiple company objectives and key results and that affected multiple groups within the company were ranked highest, she says.
To help organize the interactions between her team and the technical product managers who usher in new products and software dashboard features at Openly, Tomaro created a formal framework that paired an analyst with each product manager. The analyst could help the product manager build multi-quarter roadmaps detailing the resources required for each project and to predict how delays or re-ordering projects might affect the company. The pair could then figure out how to measure success for a product roll-out and build reporting or analysis tools to also measure success after implementation, Tomaro says.
Pairing with analysts helped the technical product managers make analytically based decisions about their initiatives while getting her team involved earlier in their planning processes. The formal framework also established “how can we get them that support that’s less ad hoc and thrown over the fence to our team,” she says. “This helped formalize it a little bit.”
Tomaro also created a premium forecasting tool by revamping a rudimentary countrywide model to analyze more state-specific variables as Openly expanded into more states. By building out the tool with a bottom-up approach, the company could add individual metrics that were driving a state’s top-line premium.
“As the years progressed, we’ve gotten more and more data, able to fill in more features and more granularity into that model to enable more precise forecasting for premium each month,” she says. The new model incorporates, for example, the total addressable market in each state, the company’s targeted percentage of that market, expected quoting per agent, quoting variances for in-state and out-of-state agents, and conversion and reject rates.
Looking ahead, Tomaro says one of her key challenges will be continuing to foster and maintain relationships within the growing company, now with more than 300 employees, about double the size when she joined.
As Openly expands into more states and the business grows more complex, it will take more effort to know what other people in the company are working on and how their projects might build on one’s own work, and vice versa, Tomaro says.
“When it’s a smaller company and there’s fewer people, it’s easier to keep in touch or make those connection points across groups and different functions,” she says. “As you add more people, you add more complexity to the business; it gets harder and harder to keep track of all that.”
