Senior Financial Analyst, Headspace Health

• 4+ 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 bookings, revenue and cash flow forecasting
• Experience analyzing revenue performance metrics such as GRR, NDR, Churn, and ARR across customer and product segments
• Experience with GTM partnership and SFDC
• 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

Desirable

• Headspace is seeking a strategic and detail-oriented Senior Financial Analyst, GTM to join our FP&A team, with a focus on Forecast to Cash
• 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
• Lead the Forecast to Cash processes - owning models and forecasts that connect bookings, revenue recognition, collections. Partner with Sales, GTM, Accounting, and FP&A teams to drive accuracy and strategic insight across annual budgeting, weekly business updates, quarterly reforecasting, and long-range planning
• Develop and evolve scalable reporting frameworks that synthesize bookings, revenue, and cash trends into actionable insights for Finance leadership and cross-functional stakeholders
• Analyze key revenue performance metrics—including GRR, NDR, Churn, and ARR—across customer, product, and channel segments to assess performance, improve forecast precision, and uncover growth opportunities
• Perform monthly variance analysis for revenue, bookings, and cash flow—translating findings into executive-ready narratives that highlight risks, performance drivers, and strategic recommendations
• Continuously optimize forecasting models and reporting processes, identifying automation and standardization opportunities to enhance 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 commissions modeling to ensure alignment across the Quote-to-Cash ecosystem
• Drive strategic insights and operational alignment between Finance and business partners, enabling data-driven decision-making across the organization