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Sherri Grasak is returning to her roots to serve as Oswald Companies’ new Market President for Pittsburgh. The Steeler nation native is thrilled to be back home in this new role to drive client growth, build on the strength of an already exceptional team and serve as the face of a community she knows and loves.
“Oswald expanded to Pittsburgh in 2022 and has built tremendous momentum,” she said. “I’m excited to take the reins and lead the next phase of growth across Pittsburgh and western Pennsylvania. Our goal is to continue to invest in Pittsburgh, while deepening client relationships with leadership excellence and outstanding client advisory.”
Growth in the Pittsburgh office has historically been driven by Employee Benefits. Grasak now plans to leverage her broad industry experience to accelerate that momentum and expand the firm’s presence across all service areas, including Property and Casualty, Employee Health and Benefits, Life Insurance, Retirement Plan Services, and other specialty practices.
A wealth of experience
Grasak brings a wealth of experience and deep market knowledge to this role. She joins Oswald from Aon, where she most recently served as Market Leader for Michigan, leading the growth and expansion of that market over the past two years. Prior to her tenure in Michigan, Grasak served as Market Leader for Pittsburgh from 2016 to 2024, building strong client relationships, developing high-performing teams, and driving sustained growth across the region. Her return to Pittsburgh marks a powerful homecoming to a market she loves and has built a strong track record.
Before joining Aon, Grasak spent 18 years at Marsh, where she held various leadership roles in property and casualty sales and brokerage. Throughout her career, she has been recognized for her ability to deliver results, inspire teams, and build meaningful relationships with clients and colleagues alike.
“We are thrilled to welcome Sherri back to Pittsburgh,” said Jessica Jung, President, Oswald Companies. “Her proven leadership, deep industry knowledge and strong client focus align with our mission to deliver exceptional outcomes for clients, while strengthening our presence in this key market.”
Building on growth momentum
Last month, the team relocated its offices to Greentree Road with expansion plans to more than double in size this year. Today, Oswald has 10 employees in Pittsburgh but plans to grow that number to 25 and expand service lines within the next two years.
Oswald has seen phenomenal growth since planting roots here in 2022. Since then, Oswald’s Pittsburgh office has grown more than 25 percent each year, and Grasak feels confident her team can keep up or even exceed that pace.
“I know this business inside and out, and I’ve been in this seat before, which gives me a clear understanding of what it takes to succeed,” said Grasak. “Growth is in my core, and I’m excited to partner with our talented colleagues to continue building on the team’s success and delivering meaningful results for our clients.”
Tripling in office size, the new 6,000-square-foot location is built for collaboration among both clients and colleagues with conference rooms and open spaces to host meetings, executive round tables and community events. And an industrial vibe is designed to foster innovation, creativity, and fun.
Oswald’s 133-year legacy
Grasak returns to her roots to call Oswald home, a company that is rooted in its core values. Through Oswald’s 133-year legacy, the person at the top may have changed—only 5 CEOs have led Oswald since 1893—but the principles and values have remained steadfast:
- Passion for excellence
- Integrity
- Resourcefulness
- Commitment to Community
These four core values are instilled in its employee-owners and demonstrated every day as the firm serves its clients and community.
Founded in 1893, Oswald Companies has grown from a Cleveland-based agency into a nationally recognized leader in risk management and insurance brokerage services with more than 500 employee-owners across 9 locations, the most recent in Pittsburgh.
Today, Oswald Companies, a Unison Risk Advisors Company, provides full-service insurance and risk management solutions, including property and casualty, employee benefits, retirement plan services, life insurance, and personal client management.
It’s a journey rooted in a deep commitment to its people, its clients and its communities and a legacy worth protecting, while remaining energized for a bright future.
“What attracted me most to Oswald Companies is a culture driven by amazing leadership and an inspirational level of collaboration and focus on clients,” said Grasak. “As employee-owners, we all have skin in the game to help a client, colleague and be accessible to the community. Oswald is a company that truly lives and breathes its core values.”
This article also appeared in the Pittsburgh Business Times.
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