Regional Sales Director, Intergrated Health

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 – Integrated Health, 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.

Expectations:

Foundational Onboarding & Certification (Q1)

• Gain full understanding of our company’s ecosystem and origin story; demonstrate mastery through executive team presentation.
• Become CP Certified in value proposition, products, services, and solutions.
• Attend in-person training at HQ and pass the final training exam.
• Conduct prospect calls and send strategic outreach emails.

Pipeline Development & Broker Activation (Q2)

• Maintain monthly prospecting calls and emails.
• Identify and contact Top broker firms.
• Activate Preferred Broker Firms (completed NDA, Certification, MEP, and agreement).
• Schedule and attend face-to-face meetings with all Preferred Brokers twice per quarter.
• Generate quotes and maintain an average of 3 First-Time Appointments (FTAs) weekly.
• Complete one SME trip (face-to-face meetings in 48 hours).
• Read The Energy Bus and present findings.

Pipeline Acceleration (Q3)

• Continue prospecting cadence:  calls &  emails monthly.
• Expand quoting to Preferred Broker Firms.
• Deliver quotes and hand-deliver proposals to brokers/clients.
• Maintain FTAs per week and one SME trip.
• Read and present insights from The Undoing Project.

Conversion & Performance Metrics (Q4)

• Maintain outreach and broker engagement cadence.
• Preferred Broker Firms quoting.
• Deliver quotes and increase face-to-face broker/client interaction.
• Achieve a close ratio.
• Conduct regular SME visits and weekly FTAs.
• Read and present key lessons from Good to Great.

High-Performance Execution (Q5)

• Achieve x Preferred Broker Firms quoting.
• quotes delivered and closed deals by end of Q5.
• Raise close ratio to 7%.
• Continue weekly FTAs and strategic SME visits.
• Maintain the rigorous engagement process to uphold Preferred Broker standards.

Key Competencies:

• ·        Prospecting Mastery: Relentless outbound effort with strategic messaging.
• ·        Broker Enablement: Ability to build, train, and activate channel partners.
• ·        Operational Discipline: Execute with consistency and precision against KPIs.
• ·        Business Acumen: Deep understanding of insurance ecosystems and employer needs.
• ·        Communication: Clear, compelling presentations to brokers and internal stakeholders.
• ·        Coachability & Learning: Eagerness to read, absorb, and apply new sales philosophies.

• 7–10 years of B2B sales experience, preferably in insurance, healthcare, or benefits consulting.
• Proven success with broker/partner development and territory management.
• 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, Marketing, Healthcare Administration, or related field

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