Senior Financial Analyst, GTM

Headspace Sourcing

1d•Hybrid

About The Position

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.

Requirements

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

Nice To Haves

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

Responsibilities

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.