Full-Time

Customer Success Manager

Updated on 9/3/2026

Oswald

Oswald

501-1,000 employees

Independent insurance brokerage and risk management

No salary listed

Richfield, OH, USA

In Person

Bachelor's

Category
Customer Experience & Support (1)
Required Skills
HIPAA
Data Analysis

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Requirements
  • A bachelor's degree in business, healthcare administration, or a related field, or equivalent experience.
  • At least 3 years of experience in customer success, account management, or a customer-facing role, preferably in the health insurance or benefits industry.
  • A Life and Health Insurance License, which the company will pay for if not already licensed.
  • A strong understanding of Individual Coverage Health Reimbursement Arrangements, healthcare benefits, and individual health insurance plans.
  • The ability to manage customer relationships and deliver exceptional service.
  • Excellent communication and interpersonal skills, including the ability to explain complex concepts clearly and concisely.
  • Strong problem-solving skills with a solution-oriented approach.
  • The ability to work in a fast-paced, dynamic environment and manage multiple priorities effectively.
  • Proficiency with customer relationship management systems, customer management tools, and data analysis.
Responsibilities
  • Guide customers through setting up and launching their Individual Coverage Health Reimbursement Arrangement plans.
  • Ensure smooth integration with customers' internal management systems and help customers understand plan features, compliance requirements, and best practices.
  • Provide appropriate plan advisory assistance during the employee plan selection process.
  • Ensure employee enrollments are processed accurately and on time.
  • Ensure all payments related to the Individual Coverage Health Reimbursement Arrangement program are made promptly, address enrollment or payment delays, and ensure timely resolution.
  • Deliver training and informational sessions to customers and their teams on plan features, regulations, and optimization strategies.
  • Serve as the primary point of contact for Individual Coverage Health Reimbursement Arrangement-related inquiries.
  • Proactively address issues, troubleshoot problems, and offer solutions to ensure customer success with their plans.
  • Manage the customer renewal process, collaborate with the Individual Coverage Health Reimbursement Arrangement Analyst team, ensure contributions are updated within the customer platform, and prepare customers for annual renewals.
  • Develop trusted relationships with key customer stakeholders, check in regularly to assess satisfaction, and identify opportunities for improvement or growth.
  • Review usage data with customers, suggest improvements, and implement changes to increase plan efficiency and cost-effectiveness.
  • Collaborate with Sales, platform technology, Analyst, Marketing, and Compliance teams to relay customer feedback, recommend improvements, and ensure an exceptional customer experience.
  • Keep customers informed about healthcare regulation changes and compliance requirements, and provide guidance to ensure plans remain compliant with federal, state, and local laws.
  • Track and report customer success metrics, including engagement, retention, and overall satisfaction, and use data to identify improvement opportunities.
Desired Qualifications
  • Experience with Individual Coverage Health Reimbursement Arrangement administration platforms or benefits management software.
  • Knowledge of healthcare regulations such as the Affordable Care Act, the Employee Retirement Income Security Act, the Health Insurance Portability and Accountability Act, and other relevant compliance frameworks.

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

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.

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.