Crumdale Specialty

VP of Sales

Crumdale Specialty

full-time

Posted on:

Location Type: Remote

Location: Pennsylvania • United States

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Job Level

Lead

About the role

  • 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
  • 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
  • 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
  • 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
  • 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
  • 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%)
Benefits
  • Medical
  • Telemedicine
  • Dental
  • Vision
  • Life, AD&D, Disability
  • 401(k)
  • Flexible Time-off
Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools
sales strategypipeline managementsales forecastingperformance analyticsmarket intelligencerevenue growthrisk financingStop-Loss underwritingself-funded health planssales enablement tools
Soft Skills
leadershipmentoringcommunicationpresentationinfluencingstrategic thinkingoperational disciplinecollaborationmotivationresults-oriented