Captive SME

About the Role

The day-to-day responsibilities of this role will involve partnering with sales directors to develop and implement sales strategies, simplifying technical components of self-funding and captives, and providing training and support to producers. The Captive SME will also be responsible for building and maintaining relationships with brokers, consultants, and other external partners, as well as coordinating with internal teams to ensure seamless execution of sales plans.

The ideal candidate for this role will have a strong background in self-funding, group captives, and stop-loss strategy, as well as experience working in a fast-paced sales environment. They will be a strong communicator and strategist, able to think critically and outside the box to drive business growth.

What You Will Do

• 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
• 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
• Develop field-ready materials that increase speed-to-proposal and close rates

What We Are Looking For

• 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
• Experience working in a fast-paced sales environment with a strong focus on growth and innovation
• Strong analytical and problem-solving skills, with the ability to think critically and outside the box

Nice to Have

• Experience working with data analytics and other sales tools to drive business growth
• Strong understanding of the healthcare industry and the challenges faced by employers
• Background in marketing or business development, with a focus on building relationships and driving sales growth
• Experience working in a remote or distributed team environment, with a strong ability to communicate and collaborate with colleagues and external partners

Benefits and Perks

• Comprehensive and supportive benefits package, including medical, dental, vision, life, AD&D, disability, and 401(k)
• Flexible time-off policy, with a focus on work-life balance and employee well-being
• Opportunities for professional growth and development, with a strong focus on innovation and continuous learning
• Collaborative and dynamic work environment, with a team of experienced and dedicated professionals
• Remote work options, with the ability to work from anywhere and create a schedule that works for you
• Access to cutting-edge sales tools and technology, with ongoing training and support to ensure success
• Recognition and reward for outstanding performance, with a focus on driving business growth and innovation

• To stand out in this role, be prepared to demonstrate a deep understanding of self-funding, group captives, and stop-loss strategy, as well as strong executive communication skills.
• Emphasize your ability to think critically and outside the box to drive business growth, and highlight any experience working in a fast-paced sales environment.
• Make sure to research Crumdale Specialty and its innovative approach to healthcare solutions, and be prepared to discuss how your skills and experience align with the company's mission and values.
• Be prepared to provide specific examples of times when you had to communicate complex concepts in a clear and concise manner, and highlight any experience working with data analytics and other sales tools.
• Consider creating a portfolio or examples of your work, such as sales strategies or training materials, to demonstrate your skills and expertise to the hiring team.
• Don't be afraid to ask questions during the interview process, and be sure to discuss any concerns or reservations you may have about the role or the company.
• Be prepared to negotiate salary and benefits, and don't be afraid to advocate for yourself and your worth as a candidate.