Oswald Companies

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.

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/

05/28/2026

Family planning is a major life milestone, and no two journeys look the same. As employees take different paths to parenthood, benefit needs continue to evolve across life stages and circumstances. Thoughtful benefit design can help organizations better align support with the real experiences employees navigate during this time.

Read more to learn about inclusive family‑planning benefits for a modern workforce: https://www.oswaldcompanies.com/media-center/creating-inclusive-family-planning-pathways-for-a-modern-workforce/?utm_campaign=coschedule&utm_source=facebook_page&utm_medium=Oswald%20Companies&utm_content=Creating%20Inclusive%20Family%20Planning%20Pathways%20for%20a%20Modern%20Workforce

05/27/2026

Personal risk often grows quietly. Second homes, additional drivers, valuables and household help can all introduce new exposures over time. These changes may not prompt an immediate insurance review, which is how gaps can form without much notice. A periodic review of policies, limits and household activities can support more informed planning conversations. Learn more here:

Personal risks can disrupt long-term financial plans more quickly than market swings. Learn how insurance considerations may help reduce surprises.

05/26/2026

When costs rise, it can be hard for employers to feel like they're in control. Read our latest blog to learn why some organizations are turning to captive insurance, which can offer more cost predictability and long-term stability compared to traditional group plans.

Discover why many employers are turning to captive insurance models for their employee benefits. Amid rising costs, captives can provide cost predictability and long-term stability compared to traditional group plans.

05/21/2026

Family offices often approach personal risk with a broader lens than traditional planning models. From asset complexity to evolving exposures, this perspective can offer valuable lessons for affluent families and advisors alike. Learn more:

Family offices increasingly manage personal risk alongside investments. Learn how insurance, liability, liquidity and cyber planning support long term stability.

05/20/2026

The Cavs Hype Team brought the energy to Oswald Tower today and we felt it. We are proud to support the Cleveland Cavaliers as their insurance and risk advisor. Let's keep the momentum going. 🏀🔥

05/15/2026

Game 6 at Rocket Arena. Cleveland is ready. As the Proud Insurance and Risk Advisor of the Cleveland Cavaliers, Oswald is proud to support the team and the energy that brings our city together. Time to Go Cavs!

05/11/2026

Life sciences companies are driving some of today's most important innovations, but that same innovation is also increasing cyber risk. From IP theft to ransomware and AI manipulation, exposures are widening as quickly as technology evolves.

Explore why the industry has become a prime target and how insurance programs are adapting to help organizations think more broadly about cyber risk. Read more here:

Learn why comprehensive insurance programs are stepping up to offer broader, more flexible and tailored protection to ensure financial stability, regulatory compliance — and investor confidence.

05/06/2026

May is National Women's Health Month, highlighting an important reality for employers today. Women make up nearly half of the workforce, and their health priorities evolve over time. From caregiving pressures to different life-stage health needs, benefits strategies play a meaningful role in how employees feel at work and at home.

Learn how employers can approach women's health in ways that go beyond benefits design and support engagement, retention, and the overall employee experience. https://www.oswaldcompanies.com/media-center/how-employers-can-support-womens-health-and-well-being-in-the-workplace/?utm_campaign=coschedule&utm_source=facebook_page&utm_medium=Oswald%20Companies&utm_content=How%20Employers%20Can%20Support%20Women%27s%20Health%20and%20Well-Being%20in%20the%20Workplace