Sales Executive, Enterprise (Evergreen) at Headspace

San Francisco, California, United States

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Not SpecifiedCompensation

Senior (5 to 8 years)Experience Level

Full TimeJob Type

UnknownVisa

Mental Health, Healthcare, Employee BenefitsIndustries

Requirements

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

Responsibilities

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
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
Lead the development of strategic solutions to technical sales challenges, partnering with Sales Ops and leadership to shape sales methodologies and standards
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 sharing best practices, coaching peers, and identifying learning opportunities to strengthen sales team effectiveness
Travel as needed (~30%) to advance key deals and attend in-person meetings or events

Skills

Key technologies and capabilities for this role

Enterprise SalesQuota OwnershipOutbound ProspectingConsultative SellingProduct DemonstrationProposal DevelopmentNegotiationCross-Functional LeadershipMentoringB2B Sales

Questions & Answers

Common questions about this position

What is the compensation structure for this Sales Executive role?

This information is not specified in the job description.

Is this Sales Executive position remote or does it require office work?

This information is not specified in the job description.

What key skills are required for the Enterprise Sales Executive role?

The role requires expertise in full-cycle enterprise sales processes including outbound prospecting, consultative pitching, negotiation, and closing high-ACV deals, cultivating relationships with senior HR and benefits leaders, cross-functional collaboration, and strategic expertise in mental health benefits.

What is the team structure like for this position at Headspace?

The role sits on the Employer Sales team, collaborating with Account Development Executives (BDRs), Consultant Relations, Marketing, Sales Ops, leadership, benefits consultants, brokers, and channel partners, while mentoring junior sellers.

What makes a strong candidate for this Sales Executive position?

Strong candidates have experience closing six and seven-figure new logo deals with large enterprises (7,500+ employees), enterprise-wide influence, cross-functional leadership, and the ability to mentor junior sellers while driving market development.

Headspace

Digital health platform for mindfulness and meditation

About Headspace

Headspace is a digital health platform focused on mindfulness and meditation, aimed at helping individuals improve their mental and physical well-being. The platform offers guided meditation sessions, daily mini-meditations, and exercises tailored for various needs such as sleep, stress, and anxiety. Users can access a limited selection of content for free, but a subscription to Headspace Plus unlocks the full range of services. This subscription model not only provides a steady revenue stream but also allows users to access comprehensive tools for mental health improvement. Headspace distinguishes itself from competitors by offering free access to its premium service for unemployed individuals, showcasing its commitment to supporting mental health during difficult times. The company's goal is to enhance the overall well-being of its users through accessible mindfulness practices.

Santa Monica, CaliforniaHeadquarters

2010Year Founded

$170.6MTotal Funding

DEBTCompany Stage

Consumer Software, HealthcareIndustries

1,001-5,000Employees

Benefits

Unlimited Vacation

Catered Lunch

Fully Paid Health Care

Competitive Salaries

Free gym membership

Risks

Increased competition from fitness apps with mental health features.

Recent layoffs may indicate financial instability or restructuring challenges.

Partnership with TikTok could expose Headspace to reputational risks.

Differentiation

Headspace offers a unique AI companion, Ebb, for personalized mental health support.

The platform provides free premium access to unemployed users, showcasing social responsibility.

Headspace's partnership with Uwill expands its reach into the higher education sector.

Upsides

Growing demand for digital mental health solutions boosts Headspace's user base.

Partnership with TikTok enhances visibility among younger demographics.

Fertility journey collection taps into a niche market, attracting new users.

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