Regional Sales Director, Employee Health Benefits

About the role

As a Regional Sales Director, 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.

Requirements

• Drive regional revenue growth by developing and executing a strategic sales plan focused on health plan solutions to include level-funded, self-funded, captive, stop-loss, pharmacy solutions, and TPA solutions.
• Cultivate and expand relationships within the limited distribution network of brokers, consultants, and agents.
• Identify, develop, and close new business opportunities while strengthening existing partner relationships.
• Educate broker partners on the full suite of health plan solutions, including stop-loss, captives, and alternative funding strategies.
• Serve as a trusted advisor to brokers and consultants by delivering data-driven insights and strategic plan design recommendations.
• Collaborate cross-functionally with underwriting, actuarial, operations, and leadership teams to deliver competitive, customized proposals.
• Lead finalist presentations, strategy meetings, and executive-level discussions with brokers and employer groups.
• Maintain a disciplined pipeline management process, providing accurate forecasting and sales reporting.
• Monitor regional market trends, competitor activity, and emerging opportunities to proactively position solutions.
• Achieve and exceed assigned sales targets, growth metrics, and profitability goals.
• Ensure alignment with underwriting discipline and long-term profitability strategy.
• Represent at industry events, conferences, and broker functions to expand brand visibility and market presence.
• Uphold a culture of alignment, innovation, and integrity in all external and internal interactions.

Qualifications

• 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.
• Entrepreneurial mindset with the ability to operate independently in a fast-paced, high-growth environment.
• Willingness to travel within assigned region as needed.

Success Metrics & KPIs

• Performance in this role will be measured by:
• Achievement of annual new business revenue targets.
• Growth in broker/consultant partnerships within assigned territory.
• Pipeline volume, velocity, and forecast accuracy.
• Case submission activity and quote-to-bind ratio.
• Profitability and underwriting alignment of sold business.
• Retention and cross-sell/upsell penetration across full solution suite.
• Contribution to regional market share growth.
• Quality of broker engagement and brand presence in the territory.

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

Please note: Crumdale Specialty is not engaging with external recruitment agencies; please refrain from contacting us regarding this position.