Crumdale Specialty

    Regional Sales Director, Health Plan Services - Employee Benefits

    Crumdale Specialty
    Posted 11/11/2025Senior Level
    Full-time
    Healthcare
    Sales
    Broker Development
    Consultative Selling
    Strategic Selling
    Territory Management

    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:

    As the Regional Sales Director – Health Plan Services - Employee Benefits, you will be a cornerstone of our growth strategy. This role demands a highly driven, organized, and strategic professional with a passion for sales, broker development, and consultative solution selling. You will be responsible for building strong broker relationships, managing a robust sales pipeline, and closing high-quality business aligned with our integrated health platform. 7–10 years of sales experience, within employee benefits, insurance, healthcare, or benefits consulting. Proven success with broker/partner development and territory management. Experience with self-funded, stop-loss, captive insurance sales environment. Strong command of consultative and strategic selling methodologies. Comfortable working in a data- and KPI-driven environment. Exceptional presentation and communication skills. Ability to travel frequently (including overnight trips and HQ training). Bachelor’s degree in Business, Healthcare Administration, or related field.

    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.

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