VP of Sales
Crumdale Specialty is seeking a dynamic and strategic Vice President of Sales to accelerate growth across our Health Plan Service Solutions portfolio. This executive will be responsible for building and executing a high‑performance sales strategy, strengthening broker and consultant partnerships, expanding distribution channels, and driving sustainable revenue growth in a rapidly evolving healthcare and risk‑financing market.
The VP of Sales will help shape Crumdale’s national go‑to‑market strategy, lead and develop a high‑impact sales team, and collaborate cross‑functionally to enhance our market presence, value proposition, and client experience.
Key Responsibilities
1. Sales Leadership & Strategy
- Build, execute, and continuously refine Crumdale’s national sales strategy across Stop‑Loss, Captive, TPA, and Specialty Benefits solutions
- Set clear sales goals, performance targets, compensation strategies, and forecasting dashboards
- Develop a disciplined pipeline management approach with strong accountability and transparency
- Identify new market opportunities, competitive advantages, and strategic partnerships
2. Team Development & Performance Management
- Recruit, lead, mentor, and scale high‑performing Regional Sales Directors within assigned territories
- Establish training programs, playbooks, and repeatable processes for sales excellence
- Foster a culture of collaboration, motivation, and results, grounded in Crumdale’s values and client‑centric mindset
3. Broker, Consultant & Partner Relationships
- Serve as a senior‑level relationship lead with key national and regional brokers, consultants and distribution partners
- Drive engagement, education, and alignment across the broker ecosystem to deepen channel partnerships
- Represent Crumdale at industry events, conferences, and partner meetings
4. Revenue Growth & Market Expansion
- Deliver consistent year‑over‑year revenue and margin growth
- Lead initiatives to expand into new regions, verticals, and product lines
- Collaborate cross functionally with Sales, Stop-Loss, Underwriting, Pharmacy, TPA, Compliance and operations teams to enhance value propositions and win new business
5. Collaboration & Cross‑Functional Alignment
- Partner with Marketing to develop strong campaigns, branded materials, sales enablement tools, and market positioning
- Work closely with Operations, Client Success, and Implementation to ensure seamless onboarding and exceptional client outcomes
- Provide ongoing market feedback to Product, Underwriting, and Executive Leadership
6. Executive Leadership & Reporting
- Own sales forecasting, performance analytics, market intelligence, and board‑level reporting
- Serve as a key member of the sales leadership team, contributing to Crumdale’s strategic planning and growth initiatives
- Ensure alignment between sales, underwriting, product, and operational roadmaps
Requirements
- 7+ years of progressive sales leadership experience in Stop‑Loss, Captives, Self‑Funded Benefits, PBM, TPA services, or related healthcare/insurance verticals
- Proven success leading a national or regional sales team with measurable revenue growth results
- Strong existing relationships with brokers, consultants, and distribution partners
- Deep understanding of self‑funded health plans, risk financing, Stop‑Loss underwriting, and employer benefits
- Exceptional communication, presentation, and influencing skills
- Highly strategic thinker with strong operational discipline and an execution‑driven mindset
- Ability to thrive in a fast‑paced, entrepreneurial, scaling environment
- Willing to travel nationally (40–60%)
Location
Remote or hybrid; travel required for training, broker meetings, team events, and industry conferences
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.