O

Oswald

Independent insurance brokerage and risk management

Client Manager - Group Benefits

Full-Time
No salary listed
Mid
Bachelor's
Pittsburgh, PA, USA
HybridHybrid work arrangement in Pittsburgh.

About the job

Requirements
  • A Bachelor's Degree in Business, Risk Management, Analytics or another related field is preferred; a high school diploma or GED, in concert with industry experience, may be used in lieu of an associate's or bachelor's degree.
  • Three to five years of employee benefits experience handling medium accounts at a high level of responsibility.
  • Executive presence and strong rapport-building and interpersonal skills for positive interaction with customers and co-workers.
  • Sound judgment and a strong critical thought process to make good decisions despite time constraints.
  • Ability to work collaboratively with internal and external stakeholders and exhibit a positive attitude.
  • Strong oral and written communication skills with clients and insurance companies.
  • Excellent organizational skills and strong financial analysis acumen.
  • Excellent working knowledge of the EPIC agency management system, carrier underwriting requirements, policy provisions, and policy changes.
  • Solid time management skills and the ability to work under pressure and meet deadlines and deliverables.
  • Ability to multitask and adapt to changing priorities.
  • Ability to contribute to team efficiency by sharing knowledge and best practices.
  • Proficiency with Microsoft Office products, including Excel and PowerPoint.
  • Ability to handle stress-related situations on a daily basis.
  • Possession of appropriate jurisdictional Life and Health licenses.
Responsibilities
  • Provide quality client management by anticipating client needs and questions, researching employee benefits programs, and managing renewals with oversight and input from senior team members.
  • Manage the client service cycle, monitor time frames, and meet renewal deadlines.
  • Participate in annual meeting planning by completing pertinent report sections and conducting research.
  • Retain and develop accounts by preparing and writing proposals, providing quote comparisons, performing benchmarking and demographic analysis, analyzing claims utilization data, conducting financial underwriting reviews, and preparing cost projection reports.
  • Provide additional client resources as needed.
  • Market renewal and new lines of coverage by creating coverage specifications, analyzing carrier quotes, negotiating with carriers, and creating and presenting coverage analyses.
  • Review policy coverage and identify cross-selling and additional revenue opportunities.
  • Develop a thorough understanding of clients' businesses, policies, practices, and industries.
  • Guide clients through the initial objective-setting process.
  • Analyze data, draw conclusions, and recommend findings to clients.
  • Respond to client needs and questions and make sound day-to-day recommendations.
  • Remain informed on technical and professional standards through company-sponsored and industry educational activities, including webinars, seminars, and conferences.
  • Communicate legislative, regulatory, and technical developments appropriately to clients.
  • Service clients in accordance with professional service standards and comply with legal and regulatory requirements.
  • Achieve a minimum rating of 90% from E&O Plus audits on all accounts.
  • Maintain a functional understanding of EPIC and update client information accordingly.
  • Ensure adequate peer review of client work, including calculations, reports, and presentations, before client delivery.
  • Delegate appropriately and provide development opportunities for co-workers.
  • Manage expectations of co-workers and clients.
  • Participate in internal and external networking activities.
  • Manage projects to meet deliverable deadlines and expectations.
  • Remain current on all assigned tasks.
  • Use awareness of the firm's service capabilities to generate client ideas, solutions, and cross-selling opportunities.

About the company

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.

Company Size

501-1,000

Company Stage

N/A

Total Funding

N/A

Headquarters

Cleveland, Ohio

Founded

1893

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Simplify Jobs

Simplify's Take

What believers are saying

  • Oswald acquired Hotaling Insurance Services and RHK Group, expanding Ohio and advisory depth.
  • January 2026 co-managing directors sharpen Health and Benefits delivery and succession.
  • Spring 2026 market reporting shows active cross-sell demand across Unison colleagues and clients.

What critics are saying

  • The 2024 Neate trade-secrets fight exposed retention leaks and client-contact vulnerability.
  • Unison's 2026 homeowner-agreement lawsuits threaten reputational spillover across Oswald's shared parent platform.
  • Aggressive regional expansion, including Pittsburgh in 2026, raises costs before revenue proves out.

What makes Oswald unique

  • Employee-owned structure and 1893 heritage still differentiate Oswald from national brokers.
  • Unison Risk Advisors gives Oswald shared scale while preserving local brand autonomy.
  • Health-and-benefits leadership pairing in 2026 signals integrated retirement and benefits execution.

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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
Sep 10th, 2026
Oswald Companies named in Business Insurance's annual Best Places to Work in Insurance 2026.

Oswald Companies named in Business Insurance's annual Best Places to Work in Insurance 2026. September 10, 2026 CLEVELAND - Sept. 10, 2026 - Oswald Companies, a Unison Risk Advisors company, is pleased to announce it has been named to the 2026 Best Places to Work in Insurance program by Business Insurance and Best Companies Group. This national program recognizes employers in the insurance industry for their performance in creating workplaces where employees can thrive and help their companies grow. The recognition reflects Oswald's employee ownership model and long-standing commitment to its core values of Passion for Excellence, Integrity, Resourcefulness and Commitment to Community. "Best Places to Work in Insurance is a special distinction because it reflects the culture of excellence our employee-owners have built together and also recognizes their impact in our risk and insurance field," said Robert Klonk, Chief Executive Officer and Chairman of Unison Risk Advisors and Oswald Companies. "We're proud of our team for earning this recognition for the second consecutive year." "At Oswald, being in good company extends beyond the relationships we build within our organization," said Jessica Jung, President, Oswald Companies. "It reflects our commitment to connecting people in ways that create value for our clients, colleagues and communities. Through collaboration, shared knowledge and meaningful engagement, we help strengthen relationships that open doors to new opportunities and support long-term success." Founded in 1893 in Cleveland, Oswald Companies has a long history in the Northeast Ohio business community, providing risk management and insurance solutions across industries. Today, Oswald has eight offices throughout Ohio and Michigan and extends its reach through Unison Risk Advisors' network of more than 40 office locations across the U.S. To learn more about the people, milestones and values that have shaped the company for more than 130 years, visit Oswald Companies: A Legacy Worth Protecting, a video series highlighting the organization's history and enduring commitment to the communities it serves. As a founding firm of Unison Risk Advisors, Oswald continues to lead the way in transforming the insurance landscape. The firm's dedication to innovation, leadership and services has made it not only as a trusted advisor to clients, but also as a beacon for talent seeking meaningful careers in the industry. This recognition is a testament to Oswald's enduring legacy and its bold vision for the future. The rankings and profiles of the recognized companies are scheduled to be published in the November issue of Business Insurance and online at BusinessInsurance.com. About the award. Best Places to Work in Insurance is an annual sponsored-content feature presented by the Custom Publishing unit of Business Insurance and Best Companies Group. The program recognizes insurance agents, brokers, carriers and other industry providers based on employee engagement and satisfaction. Best Companies Group evaluates participating employers through a two-part assessment. The first component is an employer questionnaire addressing company policies, practices and demographics. The second is a confidential employee survey focused on engagement and satisfaction. The program divides employers into three categories: small employers with 25 to 249 employees, medium employers with 250 to 999 employees and large employers with 1,000 or more employees. This year's report includes 100 companies ranging in size from 25 employees to more than 4,000. About Business Insurance. Business Insurance provides news and information for executives focused on risk and its effect on their organizations. Its coverage includes developments affecting risk managers, insurers, brokers and other insurance industry organizations. About Best Companies Group. Best Companies Group works with organizations to establish workplace recognition programs at the national, state and regional levels. Its workplace assessment uses employer questionnaires and employee surveys to identify participating organizations recognized for workplace practices and employee satisfaction.

Captive Insurance Times
Jul 28th, 2026
Pompili joins Amynta Risk Solutions as accident and health president

Pompili joins Amynta Risk Solutions as accident and health president. Amynta Risk Solutions appoints Gene Pompili as president of its accident and health and medical stop-loss division. Pompili is based in Hudson, Ohio, and provides strategic direction across underwriting, distribution, business development and long-term growth for the division. The remit covers underwriting strategy and portfolio management, the identification of new market opportunities and product innovation initiatives, and the strengthening of partnerships across the broker, carrier, managing general underwriter and employer communities. Pompili joins from ClearPoint Health, where the role was chief strategy officer. Responsibilities there covered enterprise strategy and long-term business planning, growth initiatives across captive and healthcare financing programmes, and the development of the firm's Stop-Loss Center of Excellence. Pompili was previously vice president and group benefits risk leader at Oswald Companies, leading the firm's group benefits captives practice and its consulting team. The role involved designing and managing captive and risk-sharing programmes, and advising employers on self-funded healthcare strategies and cost-containment approaches. Over the same period, Pompili served as president and treasurer of ISBC Insurance Exchange, a healthcare captive serving independent schools and colleges across the US, with oversight of governance, financial performance and risk-sharing strategy for participating member organisations. Earlier roles include president of Ringmaster Technologies, a cloud-based software platform connecting third-party administrators, agencies, carriers and managing general underwriters in the medical stop-loss market. Pompili was also regional practice leader at Roundstone, building the firm's Midwest practice for its self-funded captive stop-loss programme. The role covered captive solutions for middle-market employers, affinity groups and purchasing coalitions, including 831(b) structures, deductible reimbursement and industry-specific captives, distributed through advisor, agency and third-party administrator relationships across seven states. Pompili began a career in the sector at MetLife Insurance Company and later held a regional sales director post at Prudential Insurance Company, bringing more than 35 years across the employee benefits and specialty insurance industries. Amynta Risk Solutions is a managing general underwriter operating in the employee benefits market, with a focus on medical stop-loss. The firm is headquartered in New York.

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.