Captive SME

Crumdale Specialty

About The Position

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.

Requirements

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.

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.