Careers with Oswald

Employee Benefits

Our Culture

An ESOP Organization


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, and our partnership as a leader in The Assurex Global Network allows us to serve the risk management needs of our international clients, worldwide.

Our multi-line firm offers career opportunities in six distinct Business Units and 25 specialized Practices:

Property & Casualty    Personal Risk
Employee Benefits      Retirement Plan Services
Life Insurance             Taylor Oswald

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

Sales / Business Development        Human Resource Management
Client Management & Services       Marketing Communications & Media
Risk Management / Consulting       Information Technology
Health Management & Wellness     Accounting & Finance

Click on the “Career Opportunities” button to apply for a position that meets your qualifications and career goals!  Join our team where only the best will do!



We truly value our people!

Our “Total Rewards Package” includes a market-competitive salary, an annual pay-for-performance cash bonus for every position in the company, and an exceptional and comprehensive benefits program.  In addition, employees enjoy the opportunity to earn shares of stock in the company.

Below is a brief overview of the benefit program we provide:
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Standard Benefits

Medical & Prescription Insurance – choose from multiple PPO and HSA plan options with exceptional prescription coverage at very low employee contribution levels

Dental Insurance – a comprehensive PPO plan for preventative, basic, major restorative, and orthodontia services

Vision Insurance – a comprehensive PPO plan for annual vision exams, frames, lenses or contacts

Health & Wellness Initiative – receive reimbursement for a portion of fees paid toward an athletic club, certified wellness program, or other health-related product or service

Fitness Center – enjoy the benefit of a fully equipped on-site gym (Cleveland HQ) at no cost, and also receive a free membership at a wide variety of health clubs

Employee Assistance Plan (EAP) – no-cost counseling benefits for an employee and their immediate family members

Flexible Spending Account (FSA) – pre-tax funding for qualified health care, dependent care, and parking expenses at the IRS maximum limit allowed

Disability Insurance – receive cash compensation for eligible Short-Term and Long-Term illnesses or accidents

Life and AD&D Insurance – a fully-paid term policy providing coverage valued at two times the employee’s annualized base salary

401(k) Retirement Plan – receive a 50% employer match for each dollar deferred up to the first 6% of annual income

Employee Stock Ownership Plan (ESOP) – receive shares of stock as an Employee-Owner of Oswald Companies

Business Travel Accident Insurance – additional coverage for accidental death or dismemberment while traveling

Discount Plans – enjoy significant corporate discounts on selected products and services

Voluntary Benefits

Long Term Care Insurance – select from specialized plans for the employee and their immediate family members

Life and AD&D Insurance – additional, low-cost term life insurance for the employee and their dependents

Critical Illness & Accident Insurance – for the employee and their dependents with election during open enrollment

529 College Savings Plan – easy access to Ohio’s top rated 529 Savings Program for future education expenses

Paid Time-Off Benefits

Company Holidays – we typically recognize nine paid holidays each calendar year

Vacation Time – we calculate vacation time based upon your date-of-hire PLUS give you service credit for prior years of experience if you have held a similar position

Personal Time, Short Term Absence – we provide three personal days per calendar year

Sick Time, Short Term Absence – we provide five sick days per calendar year; unused sick time may be rolled forward each year to a maximum of 60 days (480 hours) accumulated

Ten-Year Sabbatical – you receive a paid, four-week sabbatical and a minimum cash bonus of $2,500 after serving the company for ten years

Additional Benefits

Candidate Referral Program – receive a cash bonus for the referral and successful hire of a qualified individual recommended for employment

Oswald Learning Center – we’re committed to the development of our employees and have invested in a comprehensive training platform to broaden your knowledge and advance your career with no cost to the individual

Tuition Reimbursement – receive financial support in pursuit of a formal college-degreed program




Our Core Values: PIRC

Oswald Companies is built upon four core values that we instill in our Employee-Owners and demonstrate as we perform our daily work activities and serve the community.  Known as PIRC, this acronym stands for:

  • Passion for Excellence
  • Integrity
  • Resourcefulness
  • Commitment to Community

Our Work Environment

“Our employees truly care about each other; it’s a culture where every Employee-Owner counts, regardless of their position.  We help each other and work together; it’s more of a business family than just a place to work.”  That’s how our employees describe our culture – it’s made us a “Top Workplace in Cleveland.”

We have a lot of fun too!  We’ve outfitted an on-site game room with the latest technology and some of the finest equipment.  We also sponsor a variety of activities throughout the year to demonstrate our employee appreciation like an annual company picnic, mid and year-end state-of-the-company meetings, Walnut Wednesday Parties, “who says there’s no such thing as a free-lunch” events, ice cream socials, after-work celebrations, and many other activities.

Our Commitment to Community

Oswald Companies is committed to giving back and serving the greater good.  Our new headquarters is designed to bring the community together for events and board meetings via our Oswald Conference Centre facility, which may be utilized free of charge for area nonprofit organizations.  Leaders and Employee-Owners alike are very much encouraged to be active and participate in the community through volunteering, serving on nonprofit boards and attending fundraisers.  Learn more about our Commitment to Community.

Check out a partial list of our Commitment to Community In Action:

– Adopt-A-Family: our employees provide gifts for families in need during the holiday season

– Corporate Challenge: join our team of divisional winners and compete for bragging rights

– Harvest for Hunger: we raise funds to feed families in the Greater Cleveland area

– Junior Achievement: volunteer to teach a special curriculum for Cleveland inner-city schools

– Oswald Cares: we rally together to plan and coordinate internal fundraising events and volunteer activities to support an employee experiencing difficult personal times

– Oswald’s Day of Caring – volunteer teams undertake special projects in the community

– United Way – we’re recognized as a market leader in our annual fundraising campaign


Driven by Technology & Innovation

Oswald is focused on the future, providing our Employee-Owners the tools to get there first ahead of our competition.  We invest heavily in information technology and employ applications to support optimal collaboration, mobility and scalability.

Focused on Health & Wellness

– BEAM  (Balance. Engage. Act. Motivate.): Oswald’s Wellness Committee, the BEAM Team, engages and empowers our employees to build a foundation for healthy living focused on behavior change and fitness minded programs

– On-site Health Coach: meet with our Health Coach to design, implement and track your personal health plan

– Oswald Fitness Center: enjoy the free benefit of an on-site (Cleveland), fully equipped gym

– Oswald Café: take a break and enjoy healthy choices from our vending machines and fresh fruit delivered twice a week.

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Why join an ESOP company?    

An ESOP (Employee Stock Ownership Plan) is a form of qualified retirement plan and is similar in some ways to a profit-sharing plan.  Employees receive Oswald Companies stock as we meet our profitability targets each year.  The ESOP enables our employees to be rewarded with a “personal ownership interest” in the business for their individual and team contribution.

We believe our ESOP structure contributes to our environment of cooperation and support. Because employees are owners with a personal financial stake in the overall success of the business, our workplace is very collaborative and our company is highly profitable.

It’s no surprise that having a vested interest in Oswald Companies makes a difference to our Employee-Owners.  Through goal-aligned annual planning, we work effectively and efficiently to deliver client-focused services as we accomplish our organizational objectives and achieve a healthy bottom line.

Studies show that participants in ESOPs do better, financially.  One recent study indicated that ESOP participants made 5% to 12% more in total wages, and had almost three times the retirement assets of workers who were in comparable non-ESOP companies!

At Oswald Companies, we’re a team, we enjoy our work environment and, as we achieve our goals, everyone prospers!

View the video: What employee ownership means to me.