Director of B2B Sales #0209

Our client is one of the nation’s largest telemedicine providers, offering fast, affordable virtual care to millions of patients across the country. Their platform supports acute, chronic, and lifestyle needs through virtual medical services, medication delivery, AI-enabled workflows, and proprietary care technology.

As they accelerate growth in B2B segments—including employers, staffing organizations, benefits networks, and telehealth platform partnerships—they are hiring a VP of B2B Sales to build and scale the enterprise revenue engine from the ground up.

This is a hands-on, builder role with direct ownership of enterprise sales, go-to-market execution, and early-stage partner development. You will validate ICPs, close early enterprise and broker-led deals, and create repeatable sales motions. As traction is proven, you will grow a high-performing team across multiple channels.

Core Responsibilities:

Leadership & Organizational Development

• Build, scale, and lead the B2B sales organization (AEs, SDRs, CSMs, Partner Success, Sales Engineering)
• Establish a culture of execution excellence, accountability, and data-driven decision-making
• Design compensation plans, quota structures, onboarding programs, and career ladders
• Train teams on healthcare sales methodology, PMPM pricing models, and ROI-led enterprise selling
• Personally drive early enterprise and partner-led selling motions

GTM Strategy & Execution

• Collaborate with marketing on PPC, content, events, and ABM initiatives
• Build repeatable outbound → discovery → demo → proposal → close motions
• Define ICP prioritization, segmentation, buyer personas, and channel-by-channel messaging
• Develop sales playbooks, value propositions, and presentations tailored to employers and brokers
• Establish enablement strategies for brokers and consultants

Enterprise Sales Leadership

• Work cross-functionally with Clinical Operations, Compliance, Product, and Legal
• Lead high-value sales conversations with HR leaders, founders, COOs, and benefits decision-makers
• Manage complex PMPM pricing structures, multi-state deployments, and enterprise SLAs
• Own end-to-end enterprise deal execution including discovery, proposals, negotiation, and contracting

Pipeline & Revenue Management

• Report monthly and quarterly revenue performance to the CEO and executive leadership
• Implement sales dashboards, KPIs, and performance tracking
• Own pipeline operations, forecast accuracy, and revenue pacing

Requirements

Essential:

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

Preferred:

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

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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