Oswald

Oswald

Independent insurance brokerage and risk management

About Oswald

Simplify's Rating
Why Oswald is rated
B-
Rated B on Competitive Edge
Rated B on Growth Potential
Rated C on Differentiation

Industries

Consulting

Financial Services

Company Size

501-1,000

Company Stage

N/A

Total Funding

N/A

Headquarters

Cleveland, Ohio

Founded

1893

Overview

Oswald is an independent, employee-owned insurance brokerage and risk management firm that offers property and casualty insurance, employee benefits and health management, and life insurance. Its services help clients identify, reduce, and manage risk through tailored risk management solutions. Revenue comes from brokerage fees and commissions on insurance products. Oswald serves a diverse client base including public and privately held businesses, large nonprofits, family offices, high-net-worth individuals, private equity firms, and real estate developers. The firm traces its history to 1893 and operates under a model of independent brands (now under Unison Risk Advisors) while maintaining autonomous operations.

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Simplify's Take

What believers are saying

  • Rising demand for integrated health and benefits solutions accelerates brokerage growth.
  • Strategic acquisitions like Hotaling expand service offerings and client reach nationally.
  • Thought leadership positioning through Healthcare & Risk Innovation Summit attracts premium clients.

What critics are saying

  • Unison Risk Advisors merger creates operational redundancies and erodes independent brand identity.
  • Competitors poach high-net-worth and private equity clients via superior digital platforms.
  • Hotaling integration triggers cultural clashes and talent exodus within risk management division.

What makes Oswald unique

  • Employee-owned structure with 133-year heritage builds deep client trust and retention.
  • Integrated Health and Benefits co-leadership model unifies retirement and benefits delivery.
  • Assurex Global membership provides worldwide support through network of independent brokers.

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Benefits

Health Insurance

Dental Insurance

Vision Insurance

Performance Bonus

Paid Vacation

Sabbatical Leave

Stock Options

401(k) Company Match

Flexible Work Hours

Professional Development Budget

Company News

Oswald Companies
Jan 28th, 2026
Oswald Companies Announces Deena Rini and Michael Clark as Co-Managing Directors for Health and Benefits Division

Oswald Companies announces Deena Rini and Michael Clark as Co-Managing Directors for Health and Benefits Division. CLEVELAND - January 28, 2026 - Oswald Companies, one of the country's largest independent insurance brokerage and risk management firms, is pleased to announce the appointment of Deena Rini and Michael Clark as Co-Managing Directors of its Health and Benefits Division. Rini joined Oswald in 2007 and has more than 15 years of experience, having served in multiple leadership and operational roles within Oswald's retirement plan team, most recently serving as Managing Director of Retirement Plan Services (RPS). Clark joined Oswald in 2015 as a sales consultant before advancing through several key leadership positions, most recently serving as Vice President and Benefits Sales Leader. "This evolution further positions our Health and Benefits Division for sustained growth and a unified experience for both our employees and clients," said Jessica Jung, President of Oswald Companies. "Deena and Michael bring complementary leadership and deep industry expertise that will enhance our market presence and accelerate the value we deliver to clients." "I am honored to step into this role and continue advancing the exceptional work of our Health and Benefits team," said Deena Rini. "Over my time at Oswald, I've seen how powerful it is when we align our strengths across the organization. I'm excited to partner with Michael to build an even more unified experience - one that empowers our employees, elevates leaders, and delivers meaningful, long-term value to the clients we serve." "I'm grateful for the opportunity to step into this role alongside Deena," said Michael Clark. "Our commitment is investing in, and taking care of our people, serving our clients and consistently delivering a best-in-class client experience. This co-leadership model brings benefits and retirement together in a more intentional way, allowing us to better serve our clients across our markets. Oswald is a special organization, and we look forward to building on the strong foundation established by the leaders who came before us." As Oswald continues its national expansion with Unison Risk Advisors, this co-leadership model positions them to deliver more innovative, integrated solutions that better serve the evolving needs of its clients.

Oswald Companies
Sep 29th, 2025
Hotaling & Associates Joins Oswald Companies

Hotaling Insurance Services has joined Oswald Companies, strengthening their combined offerings in insurance, risk management, and employee benefits. Learn more about this strategic partnership and what it means for clients.

Oswald Companies
Sep 4th, 2025
Oswald Companies Named in Business Insurance's Annual Best Places to Work in Insurance 2025

Oswald Companies named in Business Insurance's annual Best Places to Work in Insurance 2025.

Oswald Companies
Jun 13th, 2025
[July 30 Event] Innovate Health: Pioneering the Future of Healthcare

Oswald Company is excited to invite you to its upcoming Healthcare & Risk Innovation Summit on July 30, 2025.

Oswald Companies
May 21st, 2025
Oswald Companies Receives Award for Quality Management, Client Service for Fifth Consecutive Year

Oswald Companies, a Unison Risk Advisors company and one of the nation's largest risk management and insurance brokers, has received the E&O Plus Quality Management Award for the fifth year in a row.

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