VP of B2B Sales

Our client is one of the nation's largest telemedicine companies, delivering fast, affordable virtual care to millions of patients nationwide. Their platform supports acute, chronic, and lifestyle conditions through virtual medical services, medication delivery, AI-powered workflows, and proprietary care technology.

As they expand aggressively into B2B markets including employers, staffing organizations, benefits networks, and telehealth platform partnerships, they're seeking a VP of B2B Sales to build and scale their enterprise revenue engine from the ground up.

This is a hands-on builder role requiring direct ownership of enterprise sales, go-to-market execution, and partner development in the early phase. You'll validate ICPs, close early enterprise and broker-led deals, and establish repeatable sales motions. As traction is proven, you'll scale a high-performance organization across multiple channels.

Core Responsibilities:

Leadership & Organizational Development

• 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

GTM Strategy & Execution

• 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

Enterprise Sales Leadership

• 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

Pipeline & Revenue Management

• 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

Essential:

• 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

Preferred:

• MBA or advanced degree
• Experience at digital health or consumer health companies (Teladoc, One Medical, Amwell, Included Health, Carbon Health, Thirty Madison, Hims, Hers, Ro, Nurx, or similar)
• Established relationships with benefits brokers, consultants, TPAs, or employer networks
• Experience selling into staffing, gig economy, or distributed workforce populations
• Background negotiating enterprise SaaS or hybrid healthcare contracts

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

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