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Director, Revenue Operations

Remote - United States

About Headspace
At Headspace, our mission is to provide every person access to lifelong mental health support. We offer on-demand access to behavioral health coaching, video therapy, video psychiatry, and clinically proven self-guided content. Our team of mental health clinicians, Emmy award-winning producers, and data scientists work together to help millions of people live healthier, more productive lives.
Our enterprise business is the fastest-growing segment at Headspace, serving over 4,000 organizations and covering more than 50 million lives. We combine world-class content and care with an integrated B2B solution that includes coaching, therapy, psychiatry, and EAP services—all under one roof.

About the Director, Revenue Operations  at Headspace:

We are seeking a strategic, systems-oriented Director of Revenue Operations to lead the re-architecture of our go-to-market (GTM) systems and processes. Reporting directly to the VP of Revenue Operations, this role will manage a team of Sales, Customer Success, and Marketing Operations specialists. You will be a critical driver of operational scale, responsible for evolving our tech stack, optimizing GTM processes, and aligning cross-functional teams to deliver growth. As a department leader, you'll shape the future of our revenue operations capabilities, create multiplier effects across the organization, and develop a high-performing team that consistently delivers meticulous results.

This is a high-impact leadership role ideal for someone who thrives in fast-paced environments, can anticipate and prepare for multiple business scenarios, and has a passion for building revenue systems that enable scale and agility.

What you will do:

  • Revenue Systems Management
    • Own the strategy, implementation, and ongoing optimization of our GTM tech stack (Salesforce, HubSpot, Salesloft, Highspot) in line with evolving business needs
    • Evaluate current tools and processes; identify opportunities for automation, integration, and scale.
    • Recommend and implement new technologies to streamline workflows and improve data flow across systems.
  • Process Design & Optimization
    • Design and refine scalable, end-to-end processes across the full revenue funnel—from lead generation to renewal and expansion, in-line with emerging market trends.
    • Re-architect critical processes such as quote-to-cash to meet the needs of a maturing and evolving business.
  • Data & Analytics Infrastructure
    • Oversee data governance, CRM hygiene, and reporting integrity across all GTM systems.
    • Lead the development of dashboards, KPIs, and reporting frameworks to support real-time performance tracking and forecasting.
  • Cross-Functional Alignment
    • Set a vision for the RevOps team and act as the operational bridge between Sales, Marketing, Customer Success, and Finance; driving operational excellence across cross-functional teams
    • Enable shared definitions, seamless handoffs, and clear service level agreements (SLAs).
    • Drive adoption of new tools and processes through training, enablement, and effective change management.
  • Organizational Enablement
    • Design and implement scalable programs, processes, and policies that improve productivity across the entire GTM organization, not just within individual teams
    • Establish frameworks that allow other leaders to make better decisions faster, creating multiplicative impact beyond your direct team.
  • Talent Leadership
    • Interpret functional objectives to develop and implement a comprehensive talent strategy for the Revenue Operations department.
    • Foster a growth culture by establishing regular review processes for developmental plans and progress.
    • Empower your team to innovate and drive results through their own leadership approaches while providing consistent guidance and support.

What you will bring:

Required Skills:

  • 8+ years of experience in a Revenue Operations leadership role within a high-growth B2B organization. 4+ years people management experience. 
  • Deep understanding of B2B revenue models and the operational needs of Sales, Marketing, and Customer Success teams.
  • Demonstrated ownership of GTM systems architecture with hands-on expertise in Salesforce and HubSpot.
  • Proven track record in leading complex system implementations and large-scale process improvement initiatives.
  • Demonstrated ability to create and implement programs that anticipate and adapt to multiple future scenarios.
  • Track record of developing talent and building high-performing teams.
  • Experience leading strategic conversations and driving consensus across senior stakeholders.
  • Ability to translate industry trends into actionable strategies with company-wide impact.
  • Excellent communication, leadership, and cross-functional collaboration skills.
  • Strong problem-solving capabilities and an analytical mindset.

Preferred Skills:

  • Demonstrated success in experimenting and driving value using AI tools.
  • Background in healthcare revenue operations.
  • Salesforce Administrator certification or equivalent hands-on technical proficiency.

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 $138,600-$200,000.

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, 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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