Regional Sales Director - Captive

About Crumdale:

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:

Reporting to the Senior Vice President of Sales, the Regional Sales Director, Captives will act as Crumdale’s captive subject matter expert and sales lead responsible for generating new business revenue and growing a profitable book of business. This role will identify and develop strong broker partner relationships, work through established distribution channels of existing health plan Regional Sales Directors, and established Crumdale preferred broker partners. The focus for this sales position will be mid-sized employers (generally 25-300 enrolled employees).

The Regional Sales Director, Captive will direct and coordinate all components for the development of new business to include working across various functional areas (underwriting, marketing, operations, account management, PBM, etc.). Crumdale’s Regional Sales Director, Captives will also drive forward the orchestration and execution of captive related sales initiatives on behalf of the Senior Vice President of Sales, thereby extending the effectiveness of the organization.

Key Responsibilities:

• Identify, educate, and develop strong broker partners

• Master Crumdale’s cost containment programs and effectively apply them for brokers and employers
• Create a regional sales plan that supports the successful attainment of goals and quotas
• Execute sales techniques focused on the full sales lifecycle from lead generation to closing
• Communicate consistently across the sales team to align on goals, progress, and challenges
• Build trust and alignment across the organization to drive cohesive growth
• Drive sales of Crumdale's captive and self-funded healthcare solutions within an assigned territory
• Serve as a subject matter expert on captive insurance, stop-loss, and cost-containment strategies
• Manage a sales pipeline and consistently meet or exceed sales targets and KPIs
• Collaborate with internal underwriting, clinical, and operations teams to ensure smooth onboarding and client satisfaction
• Attend industry conferences and represent Crumdale as a trusted partner

Qualifications & Skills:

• At least five (5) years of experience in health plan captive sales; ten (10) years preferred
• Ten (10) years experience in the self-insured market preferred
• Must possess strong negotiating skills and excellent written and oral communication skills
• Bachelor’s degree preferred, or equivalent military service or work experience

• Medical, Dental, Vision, & Disability insurance 

• 401(k) 

Please note: Crumdale Specialty will not be engaging with external recruitment agencies. We kindly request that agencies refrain from contacting us regarding this position.