VP of Sales

Description
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

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
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
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
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
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
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.