Captive SME

Crumdale Specialty is seeking a Captive Subject Matter Expert (SME) to partner with Regional Sales Directors to win alternative funding opportunities specifically by turning “captive” from a conceptual idea into a clear, finance‑ready decision for employers.

This role elevates the effectiveness of our field teams by simplifying technical components of self-funding, captives, stop‑loss strategy, and cost-containment solutions. The Captive SME plays a critical part in shaping deal strategy, enabling producers, and ensuring that opportunities move efficiently from discovery to close.

Key Responsibilities:

• Serve as the subject matter expert on complex captive and alternative funding cases.
• Equip producers with concise talk tracks, discovery paths, and executive-friendly explanations of risk, funding mechanics, governance, and key tradeoffs.
• Support regional sales leaders in positioning Crumdale’s captive solutions competitively and effectively.
• Build, activate, and maintain referral networks across brokers and consultants.
• Make it simple for external partners to introduce captive strategies.
• Deliver training, tools, and confidence-building resources that expand captive pipeline opportunities.
• Coordinate with underwriting, operations, account management, and solution partners to ensure cohesive deal execution.
• Translate discovery findings into credible proposals and ensure readiness for financial and operational evaluation.
• Maintain disciplined timelines and ensure seamless handoffs into onboarding.
• Bring structure to the alternative funding sales motion with clear KPIs, next steps, and progress tracking.
• Help internal teams prioritize support based on probability to close.
• Ensure opportunities do not stall in “maybe” by driving accountability and clarity throughout the process.
• Develop field-ready materials that increase speed-to-proposal and close rates.
• Contribute to internal training, content creation, and tools that simplify complexity for both buyers and brokers.
• Represent Crumdale’s captive capabilities with clarity and authority in the market.

• Deep experience in self-funding, group captives, stop‑loss strategy, and employer funding models (mid‑market focus).
• Background working within national brokerage platforms or high‑growth consulting environments.
• Strong executive communication skills with ability to translate complex concepts into simple, defensible employer decisions.
• Proven ability to partner with frontline producers and guide complex deals through a disciplined sales process.
• Ability to orchestrate cross-functional teams from underwriting through operations to deliver accurate, timely proposals.
• High commercial acumen and strong relationship‑building skills in both direct sales and channel environments.

At Crumdale, we strive to provide a comprehensive and supportive benefits package to ensure the well-being of our employees. Our benefits include:

• Medical
• Telemedicine
• Dental
• Vision
• Life, AD&D, Disability
• 401(k)
• Flexible Time-off

Please note: Crumdale Specialty is not engaging with external recruitment agencies; please refrain from contacting us regarding this position.