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.

Business travel brings opportunity, but also a growing range of risks. As the travel landscape continues to evolve, a pr...
06/24/2026

Business travel brings opportunity, but also a growing range of risks. As the travel landscape continues to evolve, a proactive strategy can play a critical role in helping support employee safety. Read our latest blog to learn more.

Learn how employers can take a proactive approach to travel risk management. The risk landscape is constantly changing, and organizations must protect themselves and their employees.

Pharmacy is one of the biggest drivers of employer healthcare costs today and one of the most complex. What was once a p...
06/23/2026

Pharmacy is one of the biggest drivers of employer healthcare costs today and one of the most complex. What was once a predictable expense is now a rapidly shifting landscape, fueled by high-cost specialty drugs, opaque PBM contracts and limited visibility into pricing. Learn how our UnivationRx team can help employers take control by bringing clarity and transparency to the process:

Learn how our UnivationRx team can help employers take control of their pharmacy benefit strategy by bringing clarity and independence to the process.

What's the difference between simply hiring a broker and building a relationship that actually makes an impact?On The Pe...
06/16/2026

What's the difference between simply hiring a broker and building a relationship that actually makes an impact?

On The People Behind the Benefits podcast, guest Christine Karaptian, Chief People Officer of CyberMaxx, shared how working with Oswald Companies has brought a more proactive, engaged approach to the benefits conversation.

Her perspective highlights how consistency and understanding the business behind the benefits can change the dynamic entirely. When that level of proactivity is present, the relationship itself becomes part of the value and reflects the kind of work that happens in good company.

Listen to the full podcast here: https://podcasts.apple.com/us/podcast/episode-2-christine-karaptian/id1892425052?i=1000767421412&utm_campaign=coschedule&utm_source=facebook_page&utm_medium=Oswald%20Companies&utm_content=People%20Behind%20the%20Benefits%20Podcast

In private equity, rising labor and benefits costs are reshaping due diligence. Health insurance alone remains a signifi...
06/16/2026

In private equity, rising labor and benefits costs are reshaping due diligence. Health insurance alone remains a significant P&L expense, often requiring deeper analysis pre‑closing. Exploring workforce and benefits risk earlier can lead to more informed decisions across the deal lifecycle:

Today's headlines are filled with talk about inflation and rising prices. Although the recent Consumer Price Index reporting has showed a slight curve in trend, businesses will continue to deal with the balancing act of absorbing cost increases while retaining employees.The cost of labor and ben...

For 133 years, Oswald Companies has been shaped by employee ownership, strong relationships and a long-term mindset. Sma...
06/11/2026

For 133 years, Oswald Companies has been shaped by employee ownership, strong relationships and a long-term mindset. Smart Business Network magazine's June 2026 cover story reflects that story through the lens of Chairman and Chief Executive Officer Robert J. Klonk.

As Bob shared, "An owner takes better care of a customer than an employee does." That philosophy continues to influence how decisions are made and how relationships are built over time.

Read the full article here: https://www.smartbusinessemag.com/june-2026/page-24?utm_campaign=coschedule&utm_source=facebook_page&utm_medium=Oswald%20Companies&utm_content=Smart%20Business%20-%20June%202026%20Klonk%20Cover%20Story

In aging services, rising insurance costs are often shaped by everyday operational strain, not a single large loss. Work...
06/11/2026

In aging services, rising insurance costs are often shaped by everyday operational strain, not a single large loss. Workforce fatigue is one of the most overlooked drivers of claims trends and total cost of risk.

Understanding how fatigue shows up in safety data and incident patterns can help organizations identify risk earlier. Read the article here:

Workforce fatigue can signal operational risk in aging services. Learn key indicators leaders can monitor to manage claims exposure and insurance outcomes.

HR teams are balancing cost pressure with a stronger employee experience and benefits strategy is at the center of it. A...
06/08/2026

HR teams are balancing cost pressure with a stronger employee experience and benefits strategy is at the center of it.

At the National SHRM26 Conference, June 16–19 in Orlando, we're continuing the conversation around how benefits programs are adapting and where thoughtful enhancements can make a difference.

Visit us at Booth #3359 to explore Member First, Fresh Look and PulseCheck, and to discuss practical ways organizations are approaching plan design, employee experience and data‑informed decision making.

https://annual.shrm.org

Single family offices offer control and customization, while multi family offices provide shared infrastructure and oper...
06/03/2026

Single family offices offer control and customization, while multi family offices provide shared infrastructure and operational efficiency. The right structure depends less on net worth and more on factors like liability exposure, governance complexity and upcoming liquidity events. We outline how families can think about this decision through a risk‑focused lens here:

Choosing between a single or multi family office is a risk decision. Learn how structure, liability, insurance and governance shape family office strategy.

Market shifts can create opportunity, but only with the right preparation. As real estate insurance conditions begin to ...
06/02/2026

Market shifts can create opportunity, but only with the right preparation. As real estate insurance conditions begin to ease, understanding how to respond matters. Explore five practical strategies to help inform your approach in a softening market.

Explore 5 strategies to navigate a stabilizing commercial real estate insurance market, including risk management, claims strategy and coverage optimization.

This week, Oswald employee‑owners turned commitment into action. From a canned food drive at Oswald Tower to a Day of Ca...
05/28/2026

This week, Oswald employee‑owners turned commitment into action. From a canned food drive at Oswald Tower to a Day of Caring at the Greater Cleveland Food Bank, our teams supported neighbors across Northeast Ohio. In collaboration with the Cleveland Cavaliers, volunteers helped sort 12,000 pounds of food, and Oswald contributed a $14,000 donation to support the Food Bank's mission.

Read more about the experience and the impact we're making in our community: https://www.oswaldcompanies.com/media-center/oswald-employee-owners-support-greater-cleveland-food-bank-through-day-of-caring/

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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