Director, Large Deductible

Director, Large Deductible | 100% Remote (WFH) Opportunity

General Summary

The Director, Large Deductible is a senior leadership role responsible for building and running a high-performing large deductible workers’ compensation practice at EMPLOYERS. This is not a role for someone looking to maintain a steady state. It’s an opportunity for a motivated, forward-thinking professional to shape a critical program at a company in active, ambitious growth.

At its core, this role owns the full lifecycle of EMPLOYERS’ large deductible programs: program design, underwriting, loss fund administration, collateral management, financial analysis, and regulatory compliance. The Director serves as the internal subject matter expert and primary point of accountability for LD program performance, client relationships, and operational quality. Success in this role requires someone who takes initiative, thinks several steps ahead, holds themselves and their work to a high standard, and brings the flexibility to adapt as the business evolves.

This leader will partner closely with Underwriting, Finance, Actuarial, Legal, and Account Management and will be expected to engage credibly with senior leadership, large account clients, and broker partners alike. At EMPLOYERS, we value people who bring both the technical depth to get it right and the mindset to get it done.

Essential Duties and Responsibilities

• Program Management & Strategy:
  • Lead the design, development, and ongoing management of large deductible product across all applicable jurisdictions.
  • Establish and maintain program guidelines, underwriting parameters, and operational procedures specific to large deductible accounts.
  • Monitor program performance against loss fund adequacy targets and profitability benchmarks; recommend corrective actions as warranted.
  • Act as internal subject matter expert and escalation point for complex large deductible account structures, client negotiations, and loss fund disputes.
  • Evaluate and refine collateral requirements (letters of credit, surety bonds, cash collateral) in coordination with Finance and Actuarial.
  • Takes full ownership of program outcomes. Doesn’t wait to be directed. Proactively identifies gaps, proposes solutions, and follows through with accountability for results.
  • Approaches program management with a quality-first mindset. Documentation, processes, and decisions reflect rigor and a commitment to getting it right.
• Underwriting:
  • Collaborate with Underwriting leadership to develop and apply appropriate pricing models and loss development assumptions for LD accounts.
  • Review and approve LD account submissions above established authority thresholds.
  • Assess aggregate stop-loss and specific excess coverage structures to ensure adequate program protection.
  • Brings forward-thinking perspective to underwriting decisions. Considers not just the current account but how each decision shapes the portfolio over time.
  • Maintains consistent underwriting quality and discipline even under pressure to write business, holds the line with confidence and clear rationale.
• Financial Analysis & Reporting:
  • Oversee loss fund adequacy analysis across the LD portfolio, including periodic reconciliation and client reporting.
  • Develop and maintain financial models to project loss fund needs, collateral exposure, and program profitability.
  • Prepare executive-level reporting on LD product performance, trends, and risk concentrations.
  • Coordinate with Finance on loss fund accounting, reserve adequacy, and audit support.
  • Delivers financial analysis and reporting with precision and timeliness. Treats accuracy as non-negotiable and communicates results with clarity for a range of audiences.
  • Comfortable operating with ambiguity in data, knows when to dig deeper and when to make a well-reasoned call with the information available.
• Compliance & Regulatory:
  • Ensure program structures comply with applicable state regulations governing large deductible workers’ compensation arrangements.
  • Monitor regulatory changes across jurisdictions and assess impact on program design and documentation.
  • Maintain and update program filings, endorsements, and regulatory submissions as required.
  • Serve as the primary compliance liaison for LD-related regulatory inquiries and market conduct matters.
  • Stays ahead of regulatory developments rather than reacting to them, monitors the landscape continuously and raises issues early.
  • Holds compliance as a non-negotiable standard, not a checkbox. Models integrity in every program decision and client interaction.
• Stakeholder Engagement & Leadership:
  • Serve as the primary relationship manager for LD product-related interactions with large accounts, brokers, and third-party administrators.
  • Collaborate with Account Management, Loss Control, and Claims to support LD client retention and satisfaction.
  • Provide training and guidance to underwriters, account managers, and other internal stakeholders on LD program structures and administration.
  • Evaluate and manage relationships with fronting carriers and captive program partners as applicable.
  • Communicates with clarity and confidence across all levels, from internal partners to C-suite stakeholders to sophisticated broker relationships.
  • Invests in the knowledge and capability of those around them, shares expertise generously and helps others grow their understanding of the LD space.
• Other duties as assigned.

Requirements

• Bachelor’s degree in Business, Finance, Risk Management, or a related field; or equivalent professional experience.
• Equivalent combinations of education and experience may be considered.
• 7+ years of progressive experience in workers’ compensation, with meaningful exposure to large deductible program management.
• Demonstrated knowledge of LD product structures, loss fund mechanics, collateral administration, and aggregate stop-loss arrangements.
• Experience in management, or program administration environment strongly preferred.
• Comprehensive knowledge of workers’ compensation regulatory requirements across multiple jurisdictions.
• Strong financial and analytical skills, including experience building and interpreting loss projection and reserve adequacy models.
• Excellent written and verbal communication skills; ability to translate complex program mechanics for both technical and non-technical audiences.
• Demonstrated track record of taking initiative and delivering results independently. Be able to build structure and drive outcomes without step-by-step direction.
• Brings a flexible, adaptable approach to a role where priorities shift and the work continues to evolve. Resilient in ambiguity, consistent in quality.
• Preferred:
  • Advanced degree (MBA, MPA) or professional designations (CPCU, ARM, ARe, CPA) relevant to insurance or risk management.
  • Experience with captive insurance structures and fronting carrier arrangements.
  • Familiarity with reinsurance treaties and quota share/excess of loss structures applicable to program business.
  • Prior experience in a leadership or people management capacity.
  • Has sought out and applied technology, including data analytics or AI-enabled tools,to improve the quality or efficiency of their work.
• Core Competencies:
  • Strategic Thinking — Ability to assess program profitability and risk at a portfolio level and recommend proactive adjustments.
  • Analytical Rigor — Strong quantitative grounding; comfortable working with loss development data, financial models, and actuarial concepts.
  • Cross-Functional Collaboration — Effective working relationships across Underwriting, Finance, Legal, Actuarial, and Operations.
  • Regulatory Acumen — Up-to-date knowledge of state-level LD regulatory requirements and ability to navigate compliance proactively.
  • Client Orientation — Skilled at managing high-touch relationships with large accounts and broker partners.
  • Communication — Clear and credible in both written and verbal formats across all organizational levels.

Work Environment:

• Remote: This role is a remote (work from home (WFH) opportunity, and only open to candidates currently located in the United States and able to work without sponsorship.
• It requires a suitable space that provides a private and quiet workplace.
• Expected Work Hours: Schedules are set to accommodate the requirements of the position and the needs of the organization and may be adjusted as needed.
• Travel: May be required to travel to off-site location(s) to attend meetings, as necessary 

Salary Range:  $135,000 - $210,000 and a comprehensive benefits package, please follow the link to our benefits page for details! EMPLOYERS Benefits

About EMPLOYERS

As a dynamic, fast-growing provider of workers' compensation insurance and services, we are seeking a goal-oriented individual willing to put their ideas to work! 

We offer a positive, challenging work environment, combined with an opportunity to build your career as you help us grow our business, in innovative and imaginative ways that are uniquely EMPLOYERS! 

Headquartered in Nevada, EMPLOYERS attributes its long-standing success to its most valuable resource, our employees across the United States.  EMPLOYERS is known for the quality service and expertise we provide to our clients, and the exemplary work environment we provide for our employees. 

We live and breathe our core values: Integrity, Customer Focus, Collaboration, Initiative, Accountability, Innovation, and Personal Fulfillment.  These are the pillars that support how we do business with our clients as well as how we treat each other! 

At EMPLOYERS, you’ll discover an energetic environment that inspires top achievement.  As “America’s small business insurance specialist”, we have the resources, a solid reputation and an expanding nationwide identity to enrich your work/life and enhance your career. #LI-Remote About EMPLOYERS