When Melissa Winter took her first job out of college in 1998 at Sheboygan-based Acuity, she was contemplating a future career in business law.
Like many of her colleagues, Winter joined the company (then known as Heritage Mutual Insurance Co.) through its training program for recent college grads. Before she’d pursue a graduate degree, her plan was to spend some time getting a feel for the business world while also, as a claims representative, tapping into the problem solving and investigation skills she enjoyed studying while getting her undergrad at the now-shuttered Cardinal Stritch University.
Three years later, a promotion to central claims manager ultimately changed her mind.
“I stepped into that leadership role probably at about the time that I would have considered moving into graduate school of some sort, but I loved leading, loved managing a team and that really cemented my love for the insurance industry,” she said.
Today, Winter leads a workforce of roughly 1,600 employees as president of Acuity, a property and casualty insurance company that covers more than 130,000 businesses, including 300,000 commercial vehicles, and nearly half a million homes and private passenger vehicles in 31 states.
Announced in February, Winter’s promotion set in motion a leadership transition that has Acuity’s longtime head Ben Salzmann stepping aside after nearly three decades as president and chief executive officer. He will remain CEO for the next three years before passing the title on to Winter and retaining his seat on the company’s board of directors.
Meanwhile, the company continues to gain momentum in expanding its workforce, geographic footprint and market share, with written premiums totaling $2.2 billion last year. Acuity has been recognized as a top employer by various publications, including Forbes’ list of America’s Best Midsize Employers for the past three years. Securing that reputation has helped it hire at a rapid rate, with staff size increasing 18% from 2018 to 2022.
Looking back, Winter’s initial decision to stay at Acuity was rooted in what she described as a “revolution” taking hold under Salzmann’s leadership, one that ultimately transformed Acuity’s culture and performance into what defines it today.
Now, as she takes the reins, Winter sees one of her greatest responsibilities as being a “great steward and enabler” of the employee-centric, innovation-driven culture that has underpinned her 25-year career and continues to power the 98-year-old company’s future growth.
Stepping up
Winter spent seven years on the claims side of the business before moving laterally into Acuity’s internal consulting department, where she worked on claims strategy, training, process improvements and led several strategic initiatives.
She landed her first executive role in 2016 upon being named vice president of business consulting. The enterprise-focused role, overseeing strategic planning, staff functions and internal innovation teams, gave Winter a broad view of the organization and helped develop her leadership style from one centered on coaching and directing into one grounded in partnerships with other leaders driving toward a common goal, she said.
And it was within the company’s internal consulting arm where Winter developed a close working relationship with Salzmann. Through frequent collaboration on strategic planning initiatives, the two were aligned in many of their thoughts and approaches, and that helped lay the groundwork for Winter to one day carry the torch.
“We both are very passionate about innovation, very passionate about culture, looking at ways that we can stretch the organization,” she said. “I think that makes for a really strong partnership as we work through the transition years because we have a long history of open and honest communication and being able to successfully challenge one another.”
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Melissa Winter
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‘Staring down risk’
Acuity is poised for continued growth under Winter’s leadership, with plans to expand into another eight to 10 states over the next decade while also growing into new commercial business and customer segments and bolstering its presence in existing markets.
Driving this growth is a culture that “stares down risk.” Spelled out as part of Acuity’s common purpose, the mantra is somewhat of a rallying cry, said Winter.
“Insurance is about risk management and taking on risk, but we use staring down risk really to apply to more than that, that we are willing to stretch organizationally into new places, that we want to innovate, that we want to take on new challenges and step into spaces where other organizations may be held back,” she said.
In today’s post-pandemic world, that has meant embracing a hybrid workplace as a long-term strategy, “because as the world changes, our culture has to grow and thrive with it,” said Winter.
Embracing a hybrid future
Prior to the pandemic, more than 75% of Acuity’s total workforce worked exclusively from its massive headquarters building in Sheboygan, fully visible from I-43 near Kohler. The 1.2 million-square-foot campus, which features a 400-foot flagpole (flying a 140-by-70-foot American flag), 2,000-person theater, 65-foot Ferris wheel and several Dale Chihuly glass sculptures suspended from lofty lobby ceilings, is much quieter these days.
Acuity doesn’t have an official flexible work policy. Instead, it’s up to managers to work with team members to determine a schedule that works best for both the company and the individual. There are certain roles – managing cash and checks or maintaining the computer system, for example – that require employees to be on-site full time, but the company tries to “empower” its employees with choice whenever possible, said Winter.
“We believe in the culture that we have and that it is not bound by the walls of a building, rather that culture is rooted in the way our employees work with one another and in the sense of community they create,” she said.
At the same time, the company has spared no expense to bring teams together and maintain the in-office experience for those who prefer it. For starters, all employees still have their own desk space – breaking from the post-pandemic workplace trend of hoteling. And then, there are the perks. On “Free For All” Wednesdays, employees are treated to breakfast, lunch and happy hour, usually featuring some sort of entertainment. Winter said the offering has been a “big hit,” generating positive energy among the team.
Hybrid and remote work options have turned out to be a major competitive advantage for Acuity as it continues to strengthen its workforce. Not only has it helped retain existing employees who have relocated elsewhere since the pandemic, but it has also allowed the company to broaden its talent pool beyond southeastern Wisconsin.
“We get access to talent in Colorado, Georgia, across our operating territory that is otherwise talent we wouldn’t have been able to secure, which just makes us a more diverse organization and really allows us to fill our talent needs into the future,” said Winter.
