Oswald Companies

10/08/2026

Congratulations to Emma Corey on being named a 2026 Smart Business Dealmakers Rising Star in M&A by Smart Business Dealmakers. This recognition honors emerging professionals who are making an impact through leadership, innovation and a commitment to client success. We're proud to see Emma recognized among this year's honorees. ⭐ View the full list of 2026 Rising Stars: https://sbnonline.com/article/2026-northeast-ohio-smart-business-dealmakers-rising-stars/

10/08/2026

On this week's episode of Risk Vs. Reward on Cleveland Browns Daily, Dave Zastudil reflects on what stood out most from the Browns' Week 3 win over Pittsburgh: not just the performance on the field, but the energy throughout the city. As Dave put it, "It kind of had that feeling that the city believes." From the energy in the stands to the excitement across Cleveland, it's a reminder of how shared experiences can bring a community together. 🏈 Watch the full segment here: https://www.oswaldcompanies.com/cleveland-browns/

10/07/2026

Medicare's Annual Enrollment Period begins Oct. 15 and runs through Dec. 7. With changes coming to telehealth coverage, premiums and Medicare Part D costs in 2027, now is a good time to review your options. Learn what Medicare beneficiaries should know before enrollment begins: https://www.oswaldcompanies.com/media-center/medicares-2027-annual-enrollment-what-you-need-to-know/

10/05/2026

A cyberattack can do more than disrupt technology. It can halt projects, interrupt payments, expose sensitive information and create financial and operational challenges across an entire construction ecosystem. As construction firms become increasingly reliant on technology, cyber risk is becoming a growing business concern. Learn why cyber insurance, combined with proactive cybersecurity measures, plays an important role in a comprehensive risk management strategy:

Between worker injuries, equipment damage, project delays and subcontractor issues, construction companies are used to managing risk. However, one of the industry’s fastest-growing risks doesn’t necessarily happen on the jobsite.

09/28/2026

Pharmacy costs are rising, but opportunities may exist to help manage spend more effectively. Read our latest blog to learn strategies employers can explore for potential cost savings on prescription drugs in today's complex pharmacy landscape: https://www.oswaldcompanies.com/media-center/finding-opportunities-for-cost-savings-in-an-evolving-pharmacy-landscape/

09/23/2026

Risk Vs. Reward is back for the 2026-27 season on Cleveland Browns Daily!

The season is underway, and so is the return of Risk Vs. Reward on Cleveland Browns Daily featuring Dave Zastudil, former Cleveland Browns Punter and Managing Director of Property & Casualty at Oswald Companies.

As the Official Risk Advisor of the Cleveland Browns, Oswald is proud to bring Dave's unique perspective back to the show each Tuesday. Combining his NFL experience with decades of risk management expertise, Dave breaks down the biggest risk and reward moments from the previous week's game.

This week, Dave joined the program to discuss the Browns' Week 2 victory over the Tampa Bay Buccaneers, highlighting the key decisions and turning points that helped secure the win.

Be sure to tune in every Tuesday from 3-5 p.m. on Cleveland Browns Daily for another season of insights from the field and beyond.

Watch this week's segment here: https://www.oswaldcompanies.com/cleveland-browns/

09/22/2026

Insurance market conditions are no longer moving in one direction for real estate developers. While property insurance may be showing signs of moderation for well-managed assets, liability and professional lines continue to face pressure. Read more about what this two-speed market means for renewal planning and the actions developers can consider before heading into discussions with underwriters: https://www.oswaldcompanies.com/media-center/the-two-speed-insurance-market-for-real-estate-developers/?utm_campaign=coschedule&utm_source=facebook_page&utm_medium=Oswald%20Companies&utm_content=The%20Two%E2%80%91Speed%20Insurance%20Market%20for%20Real%20Estate%20Developers

09/15/2026

For family offices, insurance premiums are shaped by more than exposure and claims. Carrier strength, reinsurance costs, and industry trends all play a role. Read more here:

Why do insurance premiums stay high even with few claims? Learn how carrier performance, market forces, and pricing dynamics affect your coverage.

09/14/2026

There's no place like home to send summer out in style. From gathering at Shooters Cleveland on the Water, just across the river from our Cleveland headquarters, to cruising the Cuyahoga aboard Cle Tiki Barge and enjoying live music from Cleveland's own The Sunrise Jones band, the day was a reminder of what makes this city and our people so special. Thank you to Flats Forward Inc and the many businesses and organizations that continue to make Cleveland's riverfront a vibrant place to gather.

Most importantly, we brought together colleagues, retirees and team members from across our markets for one shared celebration of the relationships that make Oswald what it is. Thank you to everyone who joined us in sending off summer and celebrating the power of good company right here in Cleveland.

09/11/2026

In remembrance: We are deeply saddened by the passing of Jim Pender, former Chairman & CEO of Oswald Companies, and grandson of our founder, James B. Oswald. Jim's leadership, integrity, and unwavering belief in those around him shaped the culture of employee ownership that continues to define our organization today. As we honor his life and legacy, we remember a leader whose impact extended far beyond our walls to the people and communities he served.

View the full tribute: https://www.oswaldcompanies.com/media-center/remembering-jim-pender-former-chairman-ceo-of-oswald-companies/