Director, Large Deductible (Workers’ Compensation) in Chicago, Illinois at EMPLOYERS (NYSE: EIG)

Director, Large Deductible (Workers’ Compensation) - 100% Remote (U.S. Only)

EMPLOYERS is seeking a strategic, results-driven leader to build and lead our Large Deductible (LD) Workers’ Compensation program. This is a high-impact role for a professional who thrives on ownership, innovation, and shaping programs from the ground up in a growing organization.

What You’ll Do

As Director, Large Deductible, you will own the full lifecycle of our LD program—driving strategy, performance, and operational excellence. You’ll partner across the business and engage directly with senior leadership, brokers, and clients.

• Lead design, development, and execution of LD programs across jurisdictions

• Own underwriting strategy, pricing frameworks, and program guidelines

• Monitor profitability, loss fund adequacy, and portfolio performance

• Oversee collateral structures, financial modeling, and reporting

• Ensure compliance with multi-state regulatory requirements

• Act as subject matter expert and escalation point for complex accounts

• Build strong relationships with clients, brokers, and internal stakeholders

Why Join EMPLOYERS

• Fully remote, work-from-home opportunity

• Competitive salary: $120,000 – $180,000 + comprehensive benefits

• High-visibility role with the chance to shape a critical, growing program

• Collaborative, values-driven culture focused on innovation and accountability

At EMPLOYERS, we’re committed to building something better—through integrity, collaboration, and a shared drive to succeed. If you’re ready to take ownership and make a meaningful impact, we’d love to hear from you.

What You Bring

• 7+ years of workers’ compensation experience, including large deductible programs

• Strong expertise in loss funds, collateral, underwriting, and LD structures

• Proven ability to lead initiatives, influence decisions, and deliver results independently

• Advanced financial and analytical skills with a focus on accuracy and insight

• Deep understanding of multi-state regulatory requirements

• Excellent communication skills with both technical and non-technical audiences

Preferred: Advanced degree or industry designations (CPCU, ARM, etc.), experience with captives, reinsurance, or fronting carriers, and prior leadership experience.