Regional Sales Director, TPA Solutions

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.

At Crumdale, people come first. We strive to make a positive impact on the people we serve. Our company culture is rooted in alignment, innovation, and integrity.

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.

We’re looking for a driven, broker-focused sales leader who knows how to win in the self-funded health plan space, with a focus on positioning and growing our Third Party Administration (TPA) platform.

• Drive regional revenue growth by developing and executing a strategic sales plan focused on TPA solutions within the broader health plan ecosystem
• 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, with an emphasis on TPA-led plan design and administration strategy
• 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 and competitor activity 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 Crumdale at industry events and broker functions to expand market presence
• Uphold culture of alignment, innovation, and integrity

• 5+ years of successful sales experience in self-funded health plans, TPA platforms, stop-loss, or employee benefits markets
• Demonstrated success building and managing broker/consultant relationships
• Proven track record of meeting or exceeding revenue and growth targets
• Strong understanding of alternative funding, captives, cost-containment strategies, and TPA operations
• Ability to articulate complex solutions in a consultative, value-driven manner
• Experience navigating multi-stakeholder sales cycles and leading executive presentations
• Strong pipeline management and CRM proficiency
• Financial acumen with focus on profitability
• Entrepreneurial mindset and ability to operate independently
• Willingness to travel within assigned region

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.