Captive Sales Advisor

This is a fully remote position, open to applicants in United States.

📋 Description

• Crumdale Specialty is in search of a Captive Sales Advisor to collaborate with Regional Sales Directors in securing alternative funding opportunities by transforming the concept of “captive” into a definitive, finance-ready decision for employers.

• This position enhances the efficiency of our field teams by clarifying the technical aspects of self-funding, captives, stop-loss strategies, and cost-containment solutions. The Captive SME plays a vital role in developing deal strategies, empowering producers, and ensuring that opportunities progress smoothly from discovery to closure.

• **Key Responsibilities:**

• - Act as the subject matter expert on intricate captive and alternative funding cases.

• - Provide producers with succinct talk tracks, discovery pathways, and executive-friendly explanations regarding risk, funding mechanics, governance, and key trade-offs.

• - Assist regional sales leaders in effectively and competitively positioning Crumdale’s captive solutions.

• - Establish, activate, and sustain referral networks among brokers and consultants.

• - Simplify the introduction of captive strategies for external partners.

• - Offer training, tools, and resources that foster confidence and expand captive pipeline opportunities.

• - Collaborate with underwriting, operations, account management, and solution partners to ensure cohesive execution of deals.

• - Convert discovery findings into credible proposals and prepare them for financial and operational assessments.

• - Maintain disciplined timelines and facilitate seamless transitions into onboarding.

• - Bring structure to the alternative funding sales process with clear KPIs, next steps, and progress tracking.

• - Assist internal teams in prioritizing support based on the likelihood of closing deals.

• - Prevent opportunities from stalling in “maybe” by enhancing accountability and clarity throughout the process.

• - Develop field-ready materials that improve speed to proposal and closing rates.

• - Contribute to internal training, content creation, and tools that simplify complexities for both buyers and brokers.

• - Clearly and authoritatively represent Crumdale’s captive capabilities in the market.

⛳️ Requirements

• - Extensive experience in self-funding, group captives, stop-loss strategies, and employer funding models (focused on mid-market).

• - Background in national brokerage platforms or fast-growing consulting environments.

• - Exceptional executive communication skills with the ability to simplify complex concepts into clear, defensible decisions for employers.

• - Demonstrated capability to collaborate with frontline producers and navigate complex deals through a structured sales process.

• - Ability to coordinate cross-functional teams from underwriting to operations to provide accurate and timely proposals.

• - Strong commercial acumen and effective relationship-building skills in both direct sales and channel environments.

🏝️ Benefits

• At Crumdale, we are committed to offering 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 working with external recruitment agencies; we kindly ask that you do not reach out to us regarding this position.