Captive Sales Advisor

About Crumdale Specialty:

Crumdale Specialty is a diversified insurance firm providing custom, self-funded healthcare solutions to a limited distribution network of brokers, consultants, and agents nationwide. Ranked on the Inc. 5000 Fastest Growing Companies and Best Workplaces, we leverage industry expertise, superior talent, data analytics, and a disruptive mindset to manufacture, underwrite, and administer agile, transparent, and cost-saving solutions. We optimize the fragmented health benefits supply chain to reduce health benefit costs and create better outcomes for employers and employees.

At Crumdale, people come first. We strive to make a positive impact on the people we serve. We believe this starts with the passion and purpose of our team. Our company culture is rooted in alignment, innovation, and integrity.

About the Job:

Crumdale Specialty is seeking a Captive Sales Advisor 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.