Director, Revenue Operations

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 strateg