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Headspace is hiring a
RVP, Enterprise Sales

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Read by 39 job seekers.

Remote - United States

About the RVP, Enterprise Sales Role at Headspace:

We are looking for a RVP, Enterprise Sales to join our B2B Enterprise Sales team. This is an exciting career opportunity at a dynamic growth-stage company. In this role, you will advance our mission of providing every person access to lifelong mental health support by partnering with enterprise and globally oriented companies (7500-40,000 employees) to bring the Headspace suite of meditation, mindfulness, behavioral health coaching, clinical therapy, psychiatry,  and EAP solutions as increasingly vital benefits for employees. This role will uncover, develop and close opportunities, by working with prospects to understand their business goals and acting as their resource for bringing Headspace to their employee population. You will also work with cross-functional teams to help align our product roadmap and marketing strategies as a voice of the customer. If you love working with employers from a variety of industries in a continually-evolving health and benefits environment, then come and grow with us.

How your skills and passion will come to life at Headspace:

  • Work strategically with C-suite, Health, Benefits, HR, Safety and People teams to understand, guide and influence how each organization supports its employees’ mental health and well-being. 
  • Drive revenue by managing a geographically-assigned book of employer prospects in the Central States, sourcing your own and collaboratively working with dedicated sales development staff.
  • Act resourcefully as the ‘CEO’ of a multi-state enterprise region and manage the full lifecycle of each deal including: sales and prospecting activities, billing, legal, data security, technical inquiries, etc.
  • Educate employers on the value of Headspace in a thoughtful way by demonstrating tangible outcomes and research findings, while always creating an authentic and emotional connection.
  • Increasingly demonstrate practical knowledge of, and mastery with, the health, benefits, wellbeing and safety market spaces: understand trends, industry challenges, major players, and relevant products, technologies and strategies, etc.
  • Partner with Client Success to ensure great adoption, engagement and high levels of employee satisfaction/retention and strategically manage cross-sell opportunities of Headspace product lines for existing customers.
  • Serve as the voice of the customer and collect feedback to drive continuous improvement across major business areas including product, operations, sales, marketing and solutioning efforts.
  • Establish meaningful employer and consultant relationships, increase credibility as an industry thought leader in our space, and participate at applicable regional events.

What you’ve accomplished to prepare you for this role:

Required Skills:

  • You will build your Headspace sales solutioning expertise on a strong foundation of 5-7+ years work experience in an enterprise sales role, preferably in a benefits environment
  • You are adept at selling complex solutions into Benefits, HR, People and/or Healthcare teams.
  • You have a proven track record of identifying prospect needs and successfully implementing solutions with those prospects.
  • You have a demonstrated ability to repeatedly achieve or exceed sales quota.
  • You routinely provide accurate sales forecasts within your regional pipeline reports and upward to sales leadership.
  • You optimize relationship and rapport-building skills at all levels within an organization.
  • You practice strong prioritization, time management and organizational skills.
  • You achieve employer goals by always putting the customer first.
  • You take a high-energy interest in opportunities to increase customer happiness and deepen customer relationships.
  • You have character traits that include flexibility, resiliency and being willing to adapt.
  • You support the broader Headspace organization by promoting enthusiasm, positivity and high productivity in a fast-paced, metric-driven environment.
  • You are comfortable with business travel as and when needs arise.

Preferred Skills:

  • Enterprise sales experience in a benefits environment

Pay & Benefits:

The base salary range for this role is determined by a number of factors, including but not limited to skills and scope required, relevant licensure and certifications, and unique relevant experience and job-related skills. The base salary range for this role is $125,000 - $150,000.

At Headspace, cash 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, unlimited, free mental health coaching, generous parental leave, and much more. Paid performance incentives are also included for those in eligible roles. Additional details about our Total Rewards package will be provided during the recruitment process.

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. 

*Applicants with disabilities may be entitled to reasonable accommodation under the terms of the Americans with Disabilities Act and certain state or local laws. A reasonable accommodation is a change in the way things are normally done which will ensure an equal employment opportunity without imposing undue hardship on Headspace. Please inform our Talent Acquisition team by filling out this form if you need any assistance completing any forms or to otherwise participate in the application or interview process.


Headspace participates in the E-Verify Program.

Privacy Statement

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

Estimated Salary range:

Our salary intelligence, powered by our AI algorithms, has calculated an estimated range for this position between $150,000 - $200,000 . Please note that the actual salary for this position may vary, as it is dependent on various factors including but not limited to experience, location, and market dynamics.

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