Head of Sales

Pathos

Head of Sales building The Path's digital-health B2B revenue engine from zero. Closing employer, provider, and partner contracts, then documenting and scaling the sales motion.

Posted 8/6/2026full-timeSan Francisco • California • 🇺🇸 United StatesLeadWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates extensive experience in sourcing and closing six- and seven-figure deals, particularly in the digital health sector. Proven ability to build and manage a sales pipeline, develop pricing strategies, and establish a sales team in a startup environment.

Highest-signal resume keywords

10+ Years Closing Six- And Seven-Figure DealsExperience Selling Digital Health ProductsAbility To Generate Independent Sales PipelineExperience Hiring And Managing SellersCredibility With Fortune 500 CEOs

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Sourcing DealsClosing ContractsSales Strategy DevelopmentPipeline ManagementRisk IdentificationPricing StrategyOutbound ProspectingSales Playbook DocumentationNegotiationSales Cycle Analysis

Soft Skills

Autonomous WorkDiscipline In AmbiguityRelationship BuildingCommunicationPressure-Testing Strategies

Industry Keywords

Digital HealthBenefits ProductsBenefits ConsultantsEmployersEAPsHealth SystemsPayersDistribution PartnershipsClinical ProductsEvidence-Based Products

About the role

Key responsibilities & impact

Build The Path's B2B revenue engine from zero
Personally take initial deals from conversation to signature across employers, providers, and strategic partners
Convert warm introductions and outbound prospecting into signed six- and seven-figure contracts
Work with founders to determine which channels convert, at what price, and on what sales cycle
Personally sign first customers within 12 months, including paid pilots and six- and seven-figure contracts
Convert CEO-level introductions from founders and advisors into contracts
Establish evidence-based channel, pricing, and sales-cycle strategy within 12 months
Maintain an honest pipeline with real forecasts
Document the sales playbook covering targeting, pitch, pricing, proposal, and close
Hire and build the sales team once the motion is proven
Report to the CEO

Requirements

What you’ll need

10+ years personally sourcing and closing six- and seven-figure deals
Experience selling digital health or benefits products into employers
Knowledge of benefits consultants and brokers
Ability to generate an independent sales pipeline
Experience identifying and addressing deal risks including security review, legal, clinical scrutiny, and budget cycles
Credibility with Fortune 500 CEOs, celebrity founders, and billionaire investors
Ability to pressure-test pricing and channel strategy and conduct researched outbound outreach
Ability to operate autonomously and with discipline in ambiguity
Experience hiring and managing sellers
Ability to work in the office Tuesday through Thursday / 3 days per week
Currently eligible to work in the United States
Great to have: experience selling into, against, or through EAPs; relationships with benefits consultants and brokers; experience with providers, health systems, payers, or distribution partnerships; experience selling clinical or evidence-based products; experience as a first sales hire at an early-stage startup