VP of B2B Sales

Role Overview

• Personally lead early enterprise and partner-driven sales efforts
• Build, scale, and manage the B2B sales organization (AEs, SDRs, CSMs, Partner Success, Sales Engineering)
• Design compensation plans, quota structures, onboarding programs, and career ladders
• Establish a culture of execution excellence, accountability, and data-driven decision-making
• Train teams on healthcare sales methodology, PMPM pricing models, and ROI-driven enterprise selling
• Define ICP prioritization, segmentation, buyer personas, and messaging by channel
• Build repeatable outbound → discovery → demo → proposal → close motions
• Develop sales playbooks, value propositions, and presentations tailored to employers and brokers
• Collaborate with marketing on PPC, content, events, and ABM programs
• Establish broker and consultant enablement strategies
• Lead high-value sales conversations with HR leaders, founders, COOs, and benefits decision-makers
• Own end-to-end enterprise deal execution including discovery, proposals, negotiation, and contracting
• Manage complex PMPM pricing structures, multi-state deployments, and enterprise SLAs
• Work cross-functionally with Clinical Operations, Compliance, Product, and Legal
• Own pipeline management, forecasting accuracy, and revenue pacing
• Implement sales dashboards, KPIs, and performance tracking
• Report monthly and quarterly revenue performance to CEO and executive leadership

Requirements

• Bachelor's degree required (Business, Healthcare Administration, Finance, or related field preferred)
• 7–12+ years of B2B sales leadership experience in telehealth, healthtech, employer benefits, digital health, or adjacent healthcare sectors
• Proven track record building and scaling B2B revenue from early traction through meaningful ARR growth (e.g., $0–$10M, $5M–$30M+)
• Direct experience selling PMPM, PEPM, per-visit, or membership-based healthcare offerings
• Experience building and managing multi-channel sales teams (AEs, SDRs, CSMs)
• Demonstrated success closing mid-market and enterprise employer or benefits deals
• Strong understanding of healthcare compliance, clinical operations, and virtual care delivery
• Exceptional enterprise sales leadership and negotiation skills
• Deep familiarity with the employer benefits ecosystem
• Strong analytical and forecasting capabilities
• Ability to build systems, teams, and processes from scratch
• Excellent cross-functional collaboration and communication
• Thrives in fast-moving, founder-led environments
• Experience building out a sales department/team from scratch
• Experience building out and enforcing KPIs
• Able to take full ownership from day 1
• MBA or advanced degree (Preferred)
• Experience at digital health or consumer health companies (Preferred)
• Established relationships with benefits brokers, consultants, TPAs, or employer networks (Preferred)
• Experience selling into staffing, gig economy, or distributed workforce populations (Preferred)
• Background negotiating enterprise SaaS or hybrid healthcare contracts (Preferred)

Benefits

• Competitive base salary: $180,000
• $230,000 (depending on experience)
• Performance-based incentive structure (to be developed with successful candidate)
• Meaningful equity stake
• Fully remote position – work from anywhere
• Growth opportunity: Full ownership of the sales side of the business with ability to shape team structure, processes, and strategy
• Career path: Small organization with ability to make a significant impact and carve out the team to match your vision
• Aggressive expansion phase: Join at a pivotal moment as the company shifts from organic marketing growth to enterprise sales-driven growth