Career Opportunities

Click to Apply

Careers With Oswald

125 years and growing strong!

Oswald Companies is recognized as one of the nation’s most successful and admired insurance brokerage and risk consulting firms. Of the 26,400 registered brokers in the USA, our organization ranks in the top one-half of one percent of all brokers, and is among the largest privately held companies in the industry.

We serve a diverse base of clients located throughout all 50 states across our seven market offices, and our partnership as a leader in The Assurex Global Network allows us to serve the risk management needs of our international clients, worldwide.

Click on the “Career Opportunities” button to apply for a position that meets your qualifications and career goals.

Oswald is consistently recognized as an employer of choice in our communities. Check out our honors page and learn more about employee-ownership at Oswald below:

Get to know the people and passion behind Oswald Companies in our video below.

Career Paths With Oswald

Our multi-line firm offers career opportunities in four distinct business units including Property & Casualty and Personal Risk, Employee Benefits, Retirement Plan Services, Life Insurance, along with specialized practices, and our partner organization, Taylor Oswald.

We actively recruit and hire individuals pursuing successful careers in these areas:

Sales / Business Development Human Resource Management Client Management & Services
Marketing Communications & Media Risk Management / Consulting Information Technology
Operations & Facilities Management Accounting & Finance Administration
Data Analytics Health & Wellness Education & Engagement

Recruiting and retention has taken on a "Game of Thrones" approach where the competition is fierce to land the righ…

#OswaldCompanies and #OswaldCLIMBS is a proud supporter of @EngageCleveland’s #CLEYPWEEK19. With over 30 events, th…

Check out this feature via @clevelanddotcom for some familiar faces, and spaces, at Oswald Centre! "Local companies…

Thank you employee-owners! Oswald Companies Named to Top Workplaces List For The Sixth Consecutive Year…

Our Human Resources team is here for you. Contact Oswald today and apply for an open position.

Get Oswald’s Insights

Email Signup