Crumdale Specialty
insurance
CaptiveSalesAdvisor
Neural analysis suggests this role is
optimal for Mid+ candidates.
“Captive Sales Advisor at Crumdale Specialty. Skills: Captive Sales, Alternative Funding, Self-funding, Group Captives, Stop-loss Strategy, Sales Process, Producer Enablement, Deal Strategy, Cross-functional Team Orchestration. 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.”
What You'll Achieve.
Win alternative funding opportunities; Simplify technical components of self-funding, captives, stop‑loss strategy, and cost‑containment solutions; Shape deal strategy; Enable producers; Ensure that opportunities move efficiently from discovery to close; Increase speed-to-proposal and close rates; Expand captive pipeline opportunities
Industry & Context.
What They're Looking For.
Must Have
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, 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 relationship‑building skills in both direct sales and channel environments
What You'll Do.
Serve as the subject matter expert on complex captive and alternative funding cases.
Equip producers with concise talk tracks
and executive-friendly explanations of risk
Support regional sales leaders in positioning Crumdale’s captive solutions competitively and effectively.
and maintain referral networks across brokers and consultants.
Make it simple for external partners to introduce captive strategies.
and confidence-building resources that expand captive pipeline opportunities.
Coordinate with underwriting
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
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
and tools that simplify complexity for both buyers and brokers.
Represent Crumdale’s captive capabilities with clarity and authority in the market.
How You'll Work.
Team & Collaboration
Partner with Regional Sales Directors; Coordinate with underwriting, operations, account management, and solution partners; Orchestrate cross-functional teams from underwriting through operations
Communication Scope
executive communication skills; translate complex concepts into simple, defensible employer decisions; clarity and authority
Process & Methodology
Maintain disciplined timelines, Ensure seamless handoffs into onboarding, Bring structure to the alternative funding sales motion with clear KPIs, next steps, and progress tracking, Drive accountability and clarity throughout the process
Full Job Description
**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 confiden
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