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Director, Revenue Enablement

Remote - United States

About the Revenue Enablement Director at Headspace:

Headspace’s mission is to provide every person access to lifelong mental health support. We provide on-demand access to behavioral health coaching, video therapy, video psychiatry and self-guided content that’s proven to improve symptoms of depression and anxiety. Our team of experts ranges from mental health clinicians to Emmy award-winning producers and data scientists, working together as one to help millions of people around the world be healthier and more productive.

Headspace enterprise offerings combine this experience with a human-centered model of care, with coaching, therapy, psychiatry and EAP services under one roof. Our B2B business is the largest and fastest growing channel at Headspace, supporting 4,000+ enterprises and 50+ million covered lives. 

This  role will be responsible for leading the Sales Enablement function for our B2B business, supporting a team of 100+ Sales, Customer Success and Partnerships professionals and will report into the VP, Revenue Operations. This is a highly strategic role with a scope and potential to meaningfully alter Headspace’s growth trajectory. This is an IC role with a potential to build out a full team in the future.

What you will do:

  • Sales Process: Drive the vision, planning and implementation for rolling out an effective sales process, in collaboration with the GTM leadership team, for new business, renewals and partnerships. 
  • Training: Own the GTM training calendar, designing and delivering effective onboarding and continuing education with the highest impact. 
  • Content Creation and Management: Collaborate with marketing, product, and sales teams to ensure alignment on messaging, content, and sales strategies.
  • Measurement: Design and implement KPIs to track sales performance; take a data driven approach to implementing high-leverage leadership and front-line coaching programs as well as rallying cross-functional teams to deliver improvements.
  • Sales Technology: Own the maintenance of Sales Enablement tools. Collaborate closely with the RevOps systems team on the design of sales technology such as CRM.
  • Sales Culture: Collaborate with the GTM leadership in shaping the Sales culture at Headspace including having a strong pulse on the front-line team engagement and driving innovative programs to rally the teams to exceed goals. 

What you will bring:

Required Skills:

  • 8+ years of GTM experience with 5+ years in an Enablement role at a high-growth B2B company
  • Experience setting a vision, roadmap and a measurement system for the function 
  • Experience implementing MEDDPICC and exposure to other popular sales methodologies 
  • A deep understanding of CRM tools (e.g., Salesforce, HubSpot), sales engagement platforms, and other sales technologies
  • Strong written and verbal communication skills 
  • Passionate about fostering a performance driven sales culture

Preferred Skills:

  • Experience establishing a Sales Enablement function from the ground-up
  • A background in healthcare sales 
  • Direct sales or sales leadership experience in a past role

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 $140,000 - $190,000.

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

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