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 care, and innovative technology to help millions of members around the world get support that’s effective, personalized, and truly accessible whenever and wherever they need it.

At Headspace, our values aren’t just what we believe, they’re how we work, grow, and make an impact together. We live them daily: Make the Mission Matter, Iterate to Great, Own the Outcome, and Connect with Courage. These values shape our decisions, guide our collaborations, and define our culture. They’re our shared commitment to building a more connected, human-centered team—one that’s redefining how mental health care supports people today and for generations to come.

Why You’ll Love Working Here:

A mission that matters—with impact you can see and feel
A culture that’s collaborative, inclusive, and grounded in our values
The chance to shape what mental health care looks like next
Competitive pay and benefits that support your whole self

How we feel about Diversity, Equity, Inclusion and Belonging:

Headspace is committed to bringing together humans from different backgrounds and perspectives, providing employees with a safe and welcoming work environment free of discrimination and harassment. We strive to create a diverse & inclusive environment where everyone can thrive, feel a sense of belonging, and do impactful work together.

As an equal opportunity employer, we prohibit any unlawful discrimination against a job applicant on the basis of their race, color, religion, gender, gender identity, gender expression, sexual orientation, national origin, family or parental status, disability*, age, veteran status, or any other status protected by the laws or regulations in the locations where we operate. We respect the laws enforced by the EEOC and are dedicated to going above and beyond in fostering diversity across our workplace.

*Applicants with disabilities may be entitled to reasonable accommodation under the terms of the Americans with Disabilities Act and certain state or local laws. A reasonable accommodation is a change in the way things are normally done which will ensure an equal employment opportunity without imposing undue hardship on Headspace. Please inform our Talent team by filling out this form if you need any assistance completing any forms or to otherwise participate in the application or interview process.

Headspace participates in the E-Verify Program.

Privacy Statement

All member records are protected according to our Privacy Policy. Further, while employees of Headspace (formerly Ginger) cannot access Headspace products/services, they will be offered benefits according to the company's benefit plan. To ensure we are adhering to best practice and ethical guidelines in the field of mental health, we take care to avoid dual relationships. A dual relationship occurs when a mental health care provider has a second, significantly different relationship with their client in addition to the traditional client-therapist relationship—including, for example, a managerial relationship.

As such, Headspace requests that individuals who have received coaching or clinical services at Headspace wait until their care with Headspace is complete before applying for a position. If someone with a Headspace account is hired for a position, please note their account will be deactivated and they will not be able to use Headspace services for the duration of their employment.

Further, if Headspace cannot find a role that fails to resolve an ethical issue associated with a dual relationship, Headspace may need to take steps to ensure ethical obligations are being adhered to, including a delayed start date or a potential leave of absence. Such steps would be taken to protect both the former member, as well as any relevant individuals from their care team, from impairment, risk of exploitation, or harm.

For how how we will use the personal information you provide as part of the application process, please see: https://www.headspace.com/applicant-notice

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