Regional Sales Director, Employee Health Benefits

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 a Regional Sales Director, Employee Health 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.

We’re looking for a driven, broker-focused sales leader who knows how to win in the self-funded health plan space.

Requirements

Requirements

• 5+ years of successful sales experience in self-funded health plans, stop-loss, employee benefits, or related health insurance markets.
• Demonstrated success building and managing broker/consultant relationships within a defined territory.
• Proven track record of consistently meeting or exceeding revenue and growth targets.
• Strong understanding of alternative funding arrangements, captives, cost-containment strategies, and employer health plan design.
• Ability to articulate complex health plan solutions in a clear, consultative, and value-driven manner.
• Experience navigating multi-stakeholder sales cycles and leading executive-level presentations.
• Strong pipeline management and forecasting discipline with CRM proficiency.
• Financial acumen with the ability to align growth with underwriting profitability.
• Willingness to travel within assigned region as needed.

Benefits

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