[Remote] Finance Lead, Revenue & Cash Management at Headspace

United States

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Not SpecifiedCompensation

Senior (5 to 8 years), Expert & Leadership (9+ years)Experience Level

Full TimeJob Type

UnknownVisa

Technology, HealthtechIndustries

Requirements

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
Bachelor's degree in Finance, Accounting, or related field (preferred)
Software experience with Salesforce (preferred)
Experience with Health benefits/Healthcare/Mental Health/Wellness industries (preferred)
Familiarity with Adaptive Insights (preferred)
Permanently reside in the US full-time (remote in US or hybrid in SF/LA)

Responsibilities

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

Skills

Key technologies and capabilities for this role

financial modelingrevenue forecastingcash flow forecastingFP&Abudgetingvariance analysisARRGRRNDRChurnGTM commissionsrevenue recognitionExcel

Headspace

Digital health platform for mindfulness and meditation

About Headspace

Headspace is a digital health platform focused on mindfulness and meditation, aimed at helping individuals improve their mental and physical well-being. The platform offers guided meditation sessions, daily mini-meditations, and exercises tailored for various needs such as sleep, stress, and anxiety. Users can access a limited selection of content for free, but a subscription to Headspace Plus unlocks the full range of services. This subscription model not only provides a steady revenue stream but also allows users to access comprehensive tools for mental health improvement. Headspace distinguishes itself from competitors by offering free access to its premium service for unemployed individuals, showcasing its commitment to supporting mental health during difficult times. The company's goal is to enhance the overall well-being of its users through accessible mindfulness practices.

Santa Monica, CaliforniaHeadquarters

2010Year Founded

$170.6MTotal Funding

DEBTCompany Stage

Consumer Software, HealthcareIndustries

1,001-5,000Employees

Benefits

Unlimited Vacation

Catered Lunch

Fully Paid Health Care

Competitive Salaries

Free gym membership

Risks

Increased competition from fitness apps with mental health features.

Recent layoffs may indicate financial instability or restructuring challenges.

Partnership with TikTok could expose Headspace to reputational risks.

Differentiation

Headspace offers a unique AI companion, Ebb, for personalized mental health support.

The platform provides free premium access to unemployed users, showcasing social responsibility.

Headspace's partnership with Uwill expands its reach into the higher education sector.

Upsides

Growing demand for digital mental health solutions boosts Headspace's user base.

Partnership with TikTok enhances visibility among younger demographics.

Fertility journey collection taps into a niche market, attracting new users.

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