Oswald Companies

Oswald Companies Risk and Insurance Leadership since 1893.

Through our seven market locations, and family of partner companies, our “One Oswald“ approach helps individuals and businesses identify, reduce and manage their risks through our collaborative business units: property and casualty, employee benefits, personal client management, retirement plan services and life insurance.

Many organizations spend significant time evaluating healthcare, pharmacy and retirement benefits, but paid leave is oft...
08/25/2026

Many organizations spend significant time evaluating healthcare, pharmacy and retirement benefits, but paid leave is often overlooked as a strategic workforce tool. With changing employee expectations and a growing patchwork of state leave laws, now is the time to take a fresh look at your leave strategy. Learn how a proactive approach can help support employees while managing risk and resources here:

Learn about the key role paid leave plays in protecting employees' income and well-being and how employers who take a thoughtful approach to their leave programs can support employees while managing cost and risk.

What should business leaders be paying attention to as they plan for the year ahead?Join Oswald and First Financial Bank...
08/20/2026

What should business leaders be paying attention to as they plan for the year ahead?
Join Oswald and First Financial Bank on Sept. 10 at the Cleveland Yachting Club for, From the Crow's Nest: Economic Outlooks in Uncharted Waters. Hear perspectives on market trends, AI and cybersecurity from industry leaders, including Lacy Rex, Cyber Risk Solutions National Practice Leader at Unison Risk Advisors. Register by Sept. 3: https://forms.cloud.microsoft/pages/responsepage.aspx?id=Y035UcldPE-g0Q24eSn1flyTFg_IO65Mm9CYyjby7WVUMlZDU1MzMlFLMUpJVzdIVVpYQ1hMRloyWS4u&route=shorturl

Not every cyber incident begins with a technical vulnerability. Increasingly, attackers are exploiting everyday workflow...
08/19/2026

Not every cyber incident begins with a technical vulnerability. Increasingly, attackers are exploiting everyday workflows, urgency and human behavior to gain access and create disruption. For law firms, that can mean heightened risks around confidential information, client communications and business continuity.

Learn what organizations should be reviewing now: https://www.oswaldcompanies.com/media-center/cyber-extortion-and-social-engineering-what-law-firms-should-review-now/?utm_campaign=coschedule&utm_source=facebook_page&utm_medium=Oswald%20Companies&utm_content=Cyber%20Extortion%20and%20Social%20Engineering%3A%20What%20Law%20Firms%20Should%20Review%20Now

08/17/2026

highlights the important role nonprofits play in strengthening the communities where we live and work. At Oswald, our Commitment to Community is one of the core values that guides how we engage beyond the workplace. We're proud to support nonprofit organizations whose work creates opportunity, addresses local needs and helps communities thrive. Learn more about our efforts: https://www.oswaldcompanies.com/media-center/video-national-nonprofit-day-commitment-to-community-at-oswald-part-1/?utm_campaign=coschedule&utm_source=facebook_page&utm_medium=Oswald%20Companies&utm_content=%5BVideo%5D%20National%20Nonprofit%20Day%3A%20Commitment%20to%20Community%20at%20Oswald%20%28Part%201%29

Preparing heirs means more than teaching investment strategy and wealth stewardship. It also means helping them understa...
08/05/2026

Preparing heirs means more than teaching investment strategy and wealth stewardship. It also means helping them understand the risks that come with inherited wealth and how those risks can affect lifestyle, reputation and financial stability.

Read the full blog to learn how family offices can help the next generation better understand and manage the risks that often accompany inherited wealth. https://www.oswaldcompanies.com/media-center/preparing-heirs-for-risk-not-just-wealth/?utm_campaign=coschedule&utm_source=facebook_page&utm_medium=Oswald%20Companies&utm_content=Preparing%20Heirs%20for%20Risk%2C%20Not%20Just%20Wealth

  is about more than gaining experience. It's about discovering what's possible. This summer, our   challenged themselve...
07/30/2026

is about more than gaining experience. It's about discovering what's possible. This summer, our challenged themselves, contributed fresh ideas and gained firsthand insight into the work happening across Oswald. Today, we're celebrating their curiosity, growth and the impact they've made along the way.

Protecting your personal information is key to preventing identity theft. Learn how offering identity theft protection b...
07/29/2026

Protecting your personal information is key to preventing identity theft. Learn how offering identity theft protection benefits to your employees can help safeguard their personal information in a growing cyber risk landscape here: https://www.oswaldcompanies.com/media-center/safeguarding-your-employees-personal-information-with-identity-theft-protection-benefits/?utm_campaign=coschedule&utm_source=facebook_page&utm_medium=Oswald%20Companies&utm_content=Safeguarding%20Your%20Employees%27%20Personal%20Information%20with%20Identity%20Theft%20Protection%20Benefits

What if your health plan data could tell you where your next cost challenge is coming from before it shows up at renewal...
07/22/2026

What if your health plan data could tell you where your next cost challenge is coming from before it shows up at renewal? Learn how a Predictive Risk Analysis (PRA) helps employers move beyond assumptions and gain a clearer understanding of their population, risks and opportunities for action: https://www.oswaldcompanies.com/media-center/turning-your-health-plan-data-into-strategy/?utm_campaign=coschedule&utm_source=facebook_page&utm_medium=Oswald%20Companies&utm_content=Turning%20Your%20Health%20Plan%20Data%20into%20Strategy

A day full of curiosity, creativity and plenty of fun. In celebration of  , our offices across Cleveland, Cincinnati, Co...
07/17/2026

A day full of curiosity, creativity and plenty of fun. In celebration of , our offices across Cleveland, Cincinnati, Columbus and Detroit were filled with future problem-solvers, big smiles and a lot of laughs, plus a visit from Chomps and a high-energy performance from the Cleveland Cavaliers 216Stix.

From learning about insurance to ice cream and a magic show, it was a day to remember and a great reminder that what we build together extends beyond the workplace.

Address

950 Main Avenue, Suite 1800
Cleveland, OH
44113

Opening Hours

Monday 8am - 5pm
Tuesday 8am - 5pm
Wednesday 8am - 5pm
Thursday 8am - 5pm
Friday 8am - 5pm

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