Vice President of Sales

Title: VP of Sales

Location: Paoli, Pennsylvania, United States

Type: Full-time

Workplace: Fully remote

Job Description:

RemoteSalesFull time

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

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.