Finance Lead, Revenue & Cash Management

About the Finance Lead, Revenue & Cash Management at Headspace:

Headspace is seeking a strategic and detail-oriented Finance Lead, Revenue and Cash Management to join our FP&A team, with a focus on revenue, cash planning, and GTM commissions. This role will serve as a cross-functional financial partner to key stakeholders across Sales, Deal Desk, and Accounting—helping shape strategic forecasting decisions and surface data-driven insights to guide leadership decisions.

What you will do:

• Lead components of the company’s revenue, cash, and GTM commissions planning processes—owning models, partnering with cross-functional teams, and providing strategic recommendations as part of annual budgeting and quarterly reforecasting.
• Build and evolve reporting frameworks that synthesize revenue and cash trends into actionable insights for Finance leadership and cross-functional partners.
• Analyze revenue performance metrics such as GRR, NDR, Churn, and ARR across customer and product segments to support forecast accuracy and surface insights
• Perform monthly revenue and cash flow variance analysis—translating key findings, risks, and performance drivers into executive-ready insights that inform decision-making.
• Continuously evaluate and enhance forecasting and reporting processes, identifying opportunities to automate, streamline, and rebuild models to improve accuracy, scalability, and efficiency
• Serve as a strategic financial partner to Accounting, GTM, and Deal Desk—collaborating on revenue recognition nuances, complex deal structures, and commission modeling to ensure alignment with company goals.

What you will bring:

Required Skills:

• 7+ years of financial analysis and budgeting experience, including revenue, cash planning, and GTM commissions. 
• Excellent analytical and financial modeling skills, with strong attention to detail and organizational abilities 
• Deep understanding of financial principles, including cash flow forecasting, working capital management, and three statement modeling 
• Experience analyzing revenue performance metrics such as GRR, NDR, Churn, and ARR across customer and product segments
• Experience with GTM partnership and commissions planning
• Strong written and oral communication skills with experience in presenting to senior management with confidence, conviction, and credibility
• A self-starter who demonstrates initiative in shaping financial insights and improving forecasting frameworks across the business.
• Willingness to roll up your sleeves and dig into the weeds to problem solve

Preferred Skills:

• Bachelor's degree in Finance, Accounting, or related field
• Software experience with Salesforce 
• Experience with Health benefits/ Healthcare/ Mental Health/ Wellness industries
• Familiarity with Adaptive Insights

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. 

Pay & Benefits:

The anticipated new hire base salary range for this full-time position is $99,000-$138,00 + equity + benefits. 

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 ca