Sales Executive, Enterprise

Headspace

Sales Executive specializing in enterprise sales for Headspace's mental health solutions. Driving revenue and market expansion through strategic partnerships with large employers.

Posted 7/15/2026full-time🇺🇸 United StatesSeniorLead💰 $120,000 - $165,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates extensive experience in enterprise sales, particularly in the digital health and benefits solutions sector, with a strong focus on consultative selling and relationship management. Proven ability to navigate complex sales cycles and leverage industry insights to drive revenue growth and enhance organizational capabilities.

Highest-signal resume keywords

Enterprise Sales ExperienceConsultative SellingNegotiation SkillsCRM Proficiency (Salesforce)U.S. Employer Benefits Ecosystem Knowledge

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Full-Cycle Sales ManagementProposal DevelopmentPipeline ReportingSales Methodology ImplementationMarket Trend Analysis

Soft Skills

Executive PresenceRelationship BuildingMentorshipCommunication SkillsSelf-Motivation

Tools & Technologies

Salesforce

Industry Keywords

Digital HealthEmployee BenefitsMental Health SolutionsEmployee Assistance Programs (EAP)Wellbeing Trends

About the role

Key responsibilities & impact

Own and exceed your quota by closing new logo deals with employers of 7,500+ employees, selling high-ACV (Six and Seven-Figure) multi-product contracts.
Manage full-cycle enterprise sales processes including outbound prospecting, discovery, consultative pitching, product demonstration, proposal development, negotiation, and close.
Hunter who builds and drives new revenue, opens new markets, and creates new revenue streams.
Identifies strategic approaches to technical sales challenges, establishes sales standards, and leads adoption of solution-based selling across the enterprise team.
Cultivate trusted relationships with senior leaders across Human Resources, Total Rewards, Benefits, and People teams to deeply understand organizational needs and priorities.
Collaborate closely with Account Development Executives (BDRs), Consultant Relations, and Marketing to build pipeline and support coordinated regional go-to-market efforts.
Partner with key benefits consultants, brokers, and channel partners to amplify market reach and co-sell effectively.
Serve as a strategic expert in the mental health benefits space, leveraging industry trends, buyer insights, and competitive dynamics to shape your sales approach.
Provide accurate forecasting and pipeline reporting to support revenue planning and team-wide accountability.
Partner with Sales Ops and leadership to refine and implement sales excellence processes that support consistency across enterprise deals.
Identify market trends and propose innovative solutions in collaboration with cross-functional teams to support long-term business opportunities.
Represent Headspace at high-impact industry events and conferences to enhance brand presence and cultivate new enterprise relationships.
Contribute to organizational capability building by identifying skill gaps, providing mentorship, and creating development opportunities for other team members to enhance overall sales effectiveness.
Support capability-building across the team by sharing best practices, mentoring peers, and contributing to learning opportunities.
Travel as needed (~30%) to advance key deals and attend in-person meetings or events.

Requirements

What you’ll need

8+ years of experience in enterprise, digital health, or benefits solution sales with a strong track record of exceeding quotas.
Proven ability to sell complex solutions into HR/Benefits departments at large employers, ideally with deal sizes over $500,000 in annual contract value.
Deep understanding of the U.S. employer benefits ecosystem, including mental health, employee assistance programs (EAP), and wellbeing trends.
Strong consultative selling, negotiation, and executive presence with the ability to navigate long and strategic sales cycles.
Ability to manage multiple stakeholders, including HR, Finance, Procurement, and external brokers/consultants.
Demonstrated ability to identify process gaps and implement improved sales methodologies that enhance team effectiveness and customer outcomes.
Experience applying design thinking principles to sales challenges, with the ability to challenge assumptions and continuously improve sales approaches.
Excellent communication skills—both written and verbal—and comfort developing business cases and delivering compelling presentations.
Highly self-motivated, organized, and goal-oriented with a bias for action in a fast-paced, high-growth environment.
Comfortable using CRM tools like Salesforce to manage pipeline and forecast accurately.

Benefits

Comp & perks

comprehensive healthcare coverage
monthly wellness stipend
retirement savings match
lifetime Headspace membership
generous parental leave