Workers' Compensation Practice Leader

Are you a workers’ compensation leader who thrives on helping organizations reduce risk, improve outcomes, and build smarter long-term strategies?

R&R Insurance Services, one of the Midwest's largest independently owned insurance agencies, is seeking a Workers’ Compensation Practice Leader to shape strategy, drive growth, and elevate outcomes across our practice.

This role is ideal for a workers' compensation professional who combines deep technical expertise with a consultative approach to risk management, client strategy, analytics, and business development. You'll help shape a growing specialty practice, influence client outcomes, and expand R&R's expertise across complex workers' compensation programs.

What You'll Do

Practice Leadership

• Lead the strategic direction and continued growth of R&R’s practice.
• Develop tools, resources, and best practices that strengthen consistency and service delivery across the organization.
• Serve as the agency’s go-to expert on strategy, trends, and emerging best practices.

Client & Market Strategy

• Partner with producers, service teams, and clients to develop innovative risk management strategies.
• Advise middle-market and large commercial clients on program structure, loss trends, total cost of risk, and performance improvement opportunities.
• Support large-account renewal strategies and help clients achieve stronger retention, financial, and operational outcomes.
• Provide expertise in multi-state exposures, captive programs, high-hazard industries, niche programs, and pool exit strategies.
• Monitor market trends, carrier appetite, regulatory developments, and emerging issues to inform strategic guidance.
• Assist with carrier negotiations and placement strategies for complex and specialty programs.

Business Development & Collaboration

• Collaborate with internal analytics teams to expand reporting, benchmarking, and data-driven insights.
• Support business development efforts through prospect meetings, presentations, and growth initiatives.
• Build strong partnerships with clients, prospects, carrier partners, and internal stakeholders to drive measurable value.

What We're Looking For

• 8+ years of experience in workers’ compensation, risk management, underwriting, claims, brokerage, consulting, or a related field.
• Deep expertise in program design, claims management, loss control, and regulatory considerations across complex client environments.
• Proven success developing and executing strategies that improve client outcomes and drive measurable business results.
• Strong analytical and financial acumen, with the ability to interpret claims, operational, and loss data to inform recommendations.
• Executive-level communication and presentation skills, with the ability to influence clients, prospects, carrier partners, and internal stakeholders.
• Demonstrated ability to build trusted relationships and collaborate effectively across sales, service, analytics, and leadership teams.
• Active Property & Casualty license, or ability to obtain within 90 days of hire.
• Bachelor’s degree in Risk Management, Business Administration, or a related field preferred.
• Experience supporting middle-market and large commercial accounts preferred.
• Exposure to complex program structures such as multi-state risks, captives, high-hazard industries, niche programs, or pool exits preferred.

Why R&R?

As an independent, family-owned agency, R&R Insurance combines the resources and capabilities of a national brokerage with the flexibility, culture, and client-first mindset of a privately held organization. Here, you’ll have the opportunity to shape strategy, influence outcomes, and help build a growing specialty practice with the support of a collaborative, well-resourced team.