Sales Executive, Enterprise (Evergreen) Remote - United States; San Francisco - Hybrid; Santa M[...]

About the Sales Executive, Enterprise at Headspace

The Sales Executive, Enterprise Sales sits on our Employer Sales team, which is focused on bringing Headspace’s full suite of mental health and wellbeing solutions to large enterprise employers globally. This team is on the frontlines of advancing our mission to transform the health and happiness of the world, one workplace at a time. With growing demand for integrated, evidence-based benefits, we’re expanding our enterprise sales force to drive meaningful growth. This enterprise role operates at a senior level while focusing on market development. The position requires enterprise-wide influence, cross-functional leadership, and the ability to mentor junior sellers as part of developing sales capabilities across the organization. This is an exciting opportunity to shape how the largest employers in the world support their people—and to directly contribute to the continued success of Headspace’s B2B business.

What you will do :

• 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.
• Identify and propose strategic approaches to technical sales challenges affecting the enterprise team, establish sales standards, and drive adoption of solution-based selling methodologies
• 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.
• Travel as needed (~30%) to advance key deals and attend in-person meetings or events.

What you will bring :

Required Skills :

Preferred Skills :

Location :

We are currently hiring this role remotely in the US and Hybrid for San Francisco (SF) and Los Angeles (LA). Candidates must permanently reside in the US full-time. For candidates with a primary residence in the greater SF and LA areas, this role will follow our hybrid model. You’ll work 3 days per week from our office, allowing for impactful in-office collaboration and connection, while enjoying the flexibility of remote work for the rest of the week. Your recruiter will share more details about our hybrid model.

The anticipated new hire base salary range for this full-time position is $115,000-$150,000 + quarterly variable + equity + benefits. The annual on-target earnings for this role is $230,000-$300,000 (at 100% quota attainment)

Our salary ranges are based on the job, level, and location, and reflect the lowest to highest geographic markets where we are hiring for this role within the United States. Within this range, individual compensation is determined by a candidate’s location as well as a range of factors including but not limited to : unique relevant experience, job-related skills, and education or training. Your recruiter will provide more details on the specific salary range for your location during the hiring process.

At Headspace, base salary is but one component of our Total Rewards package. We’re proud of our robust package inclusive of : base salary, stock awards, comprehensive healthcare coverage, monthly wellness stipend, retirement savings match, lifetime Headspace membership, generous parental leave, and more. Additional details about our Total Rewards package will be provided during the recruitment process.

About Headspace

Headspace exists to provide every person access to lifelong mental health support. We combine evidence-based content, clinical care, and innovative technology to help millions of members around the world get support that’s effective, personalized, and truly accessible whenever and wherever they need it.

At Headspace, our values aren’t just what we believe, they’re how we work, grow, and make an impact together. We live them daily : Make the Mission Matter, Iterate to Great, Own the Outcome, and Connect with Courage. These values shape our decisions, guide our collaborations, and define our culture. They’re our shared commitment to building a more connected, human-centered team—one that’s redefining how mental health care supports people today and for generations to come.

Why You’ll Love Working Here :

How we feel about Diversity, Equity, Inclusion and Belonging :

Headspace is committed to bringing together humans from different backgrounds and perspectives, providing employees with a safe and welcoming work environment free of discrimination and harassment. We strive to create a diverse & inclusive environment where everyone can thrive, feel a sense of belonging, and do impactful work together.

As an equal opportunity employer, we prohibit any unlawful discrimination against a job applicant on the basis of their race, color, religion, gender, gender identity, gender expression, sexual orientation, national origin, family or parental status, disability, age, veteran status, or any other status protected by the laws or regulations in the locations where we operate. We respect the laws enforced by the EEOC and are dedicated to going above and beyond in fostering diversity across our workplace.

All member records are protected according to our Privacy Policy. Further, while employees of Headspace (formerly Ginger) cannot access Headspace products / services, they will be offered benefits according to the company's benefit plan. To ensure we are adhering to best practice and ethical guidelines in the field of mental health, we take care to avoid dual relationships. A dual relationship occurs when a mental health care provider has a second, significantly different relationship with their client in addition to the traditional client-therapist relationship—including, for example, a managerial relationship.

As such, Headspace requests that individuals who have received coaching or clinical services at Headspace wait until their care with Headspace is complete before applying for a position. If someone with a Headspace account is hired for a position, please note their account will be deactivated and they will not be able to use Headspace services for the duration of their employment.

Further, if Headspace cannot find a role that fails to resolve an ethical issue associated with a dual relationship, Headspace may need to take steps to ensure ethical obligations are being adhered to, including a delayed start date or a potential leave of absence. Such steps would be taken to protect both the former member, as well as any relevant individuals from their care team, from impairment, risk of exploitation, or harm.

For how how we will use the personal information you provide as part of the application process, please see : https : / / www.headspace.com / applicant-notice

Create a Job Alert

Interested in building your career at Headspace? Get future opportunities sent straight to your email.

Apply for this job

First Name

Last Name

Preferred First Name

Email

Phone

Country

Phone

Resume / CV

Enter manually

Accepted file types : pdf, doc, docx, txt, rtf

Enter manually

Accepted file types : pdf, doc, docx, txt, rtf

Employment

Title

Select...

Start date year

End date month

End date year

Current role

Do you now, or will you at any point in the future, require visa sponsorship to work in the United States? Please note that we are unable to provide visa sponsorship for this position at this time. All applicants must have the right to work in the US without requiring sponsorship.

Are you based in the greater San Francisco or Los Angeles area?

For candidates with a primary residence in the greater SF and LA areas, this role will follow our hybrid model. You’ll work 3 days per week from our office, allowing for impactful in-office collaboration and connection, while enjoying the flexibility of remote work for the rest of the week. Your recruiter will share more details about our hybrid model.

US Custom Demographic Survey

In our company-wide effort to continue to prioritize diversity and inclusion, we invite candidates to respond to both the EEOC Voluntary Self-Identification survey as well as a custom self-identification survey as a part of the application process. The EEOC survey helps us remain compliant with government reporting requirements (full information and instructions below). We have also created custom self-identification demographic questions to expand upon specific categories, offering more inclusive options that more accurately reflect the diverse global workforce. This data helps us to better understand how our DEIB efforts are tracking across various measures. Aggregated personal data will be reported on and shared with the necessary stakeholders as needed. This data will be scrubbed of all possible identifying information, is maintained in a confidential file and will not be considered in the hiring process.

If you would like to identify as a specific race, or ethnicity, please choose among the list of common racial / ethnic groups. (Select all that apply)

If you would like to identify a specific gender, please choose from the following :

Do you identify as a veteran or someone with a background in the armed forces? (Note : This includes any armed forces globally.)

Voluntary Self-Identification

For government reporting purposes, we ask candidates to respond to the below self-identification survey. Completion of the form is entirely voluntary. Whatever your decision, it will not be considered in the hiring process or thereafter. Any information that you do provide will be recorded and maintained in a confidential file.

As set forth in Headspace’s Equal Employment Opportunity policy, we do not discriminate on the basis of any protected group status under any applicable law.

If you believe you belong to any of the categories of protected veterans listed below, please indicate by making the appropriate selection. As a government contractor subject to VEVRAA, we request this information to measure the effectiveness of outreach and positive recruitment efforts. Classification of protected categories is as follows :

A "disabled veteran" is one of the following : a veteran of the U.S. military, ground, naval or air service who is entitled to compensation (or who but for the receipt of military retired pay would be entitled to compensation) under laws administered by the Secretary of Veterans Affairs; or a person who was discharged or released from active duty because of a service-connected disability.

A "recently separated veteran" means any veteran during the three-year period beginning on the date of such veteran's discharge or release from active duty in the U.S. military, ground, naval, or air service.

An "active duty wartime or campaign badge veteran" means a veteran who served on active duty in the U.S. military, ground, naval or air service during a war, or in a campaign or expedition for which a campaign badge has been authorized under the laws administered by the Department of Defense.

An "Armed forces service medal veteran" means a veteran who, while serving on active duty in the U.S. military, ground, naval or air service, participated in a United States military operation for which an Armed Forces service medal was awarded pursuant to Executive Order 12985.

Select...

Voluntary Self-Identification of Disability

Form CC-305

Page 1 of 1

OMB Control Number 1250-0005

Expires 04 / 30 / 2026

Why are you being asked to complete this form?

We are a federal contractor or subcontractor. The law requires us to provide equal employment opportunity to qualified people with disabilities. We have a goal of having at least 7% of our workers as people with disabilities. The law says we must measure our progress towards this goal. To do this, we must ask applicants and employees if they have a disability or have ever had one. People can become disabled, so we need to ask this question at least every five years.

Completing this form is voluntary, and we hope that you will choose to do so. Your answer is confidential. No one who makes hiring decisions will see it. If you want to learn more about the law or this form, visit the U.S. Department of Labor’s Office of Federal Contract Compliance Programs (OFCCP) website at www.dol.gov / ofccp.

How do you know if you have a disability?

A disability is a condition that substantially limits one or more of your “major life activities.” If you have or have ever had such a condition, you are a person with a disability. Disabilities include, but are not limited to :

Disability Status Select...

PUBLIC BURDEN STATEMENT : According to the Paperwork Reduction Act of 1995 no persons are required to respond to a collection of information unless such collection displays a valid OMB control number. This survey should take about 5 minutes to complete.

#J-18808-Ljbffr