About the VP, Strategic Finance at Headspace:
We’re entering a pivotal phase at Headspace, refining our strategy, reinforcing our operational rigor, and laying the foundation for scalable, high-impact growth. As VP of Strategic Finance, you will play a central role in this transformation.
Reporting to the CFO, you’ll lead high-impact initiatives that reshape how we allocate resources, go to market, and invest in long-term innovation. This is a change agent role, grounded in financial insight, market trends and informed by deep operating context.
You will partner cross-functionally with executives, GTM, People, Product, Legal, Operations, and Engineering to drive company-wide improvements in structure, efficiency, and growth. From capital strategy to pricing to AI enablement, your remit spans both optimization and future-building.
You will work closely with the VP of FP&A (who oversees forecasting, planning, and business performance) and VP of Accounting to ensure strategic alignment while owning discrete transformation programs end to end.
What you will do:
- Support Strategic Repositioning: Using industry knowledge, market research and past operating experience to work with CEO, CFO and Executive Team on crafting an optimal strategy for the Company.
- Optimize Operations: Using deep financial analysis and market benchmarking, lead comprehensive review and reorganization of capital allocation in the company. Identify structural inefficiencies and deploy capital for growth.
- Improve GTM Motion: Architect a focused go-to-market operating model in partnership with the GTM leads. Help stand up and run a Deal Desk and Pipeline review process. Overhaul and maintain sales incentive plans, and partner closely with GTM leadership on coverage models and customer segmentation.
- AI Enablement: Spearhead modernization of the finance function, leading the evaluation, prioritization, and implementation roadmap for AI and automation tools.
- M&A Capital Strategy: Work with CFO to evaluate M&A opportunities and use external market learnings to help drive corporate strategy and product strategy. Raise debt and equity capital to maintain Company operations and fund growth.
- Executive Influence: Act as a key thought partner to CFO and Executive Leadership Team (ELT) on corporate strategy, resource planning, and high-stakes tradeoffs.
- Lead High Performance Team: Lead and grow a high-performance team, including senior ICs and project leads. Define team structure, coach for scale, and oversee hiring, performance, and development planning aligned with business needs.
- Cross-Functional Leadership: Drive project management, alignment and accountability across Finance, Legal, People, GTM, Engineering, Product and Operations on strategic initiatives.
What you will bring:
Required Skills:
- 10-15+ years of experience in Strategic Finance, Corporate Development, Investment Banking, Consulting, or transformation roles.
- Experience within a digital health company.
- Strong ability to handle ambiguity and bring structure to ambiguity.
- Demonstrated success driving strategy, org redesigns, cost transformations, or GTM operating model shifts.
- Strong grasp of B2C and/or hybrid B2C/B2B business models and unit economics.
- Deep analytical toolkit: financial modeling, scenario planning, NPV/ROI frameworks.
- Ability to lead without authority and build consensus across diverse functions.
- Exceptional executive communication skills: synthesize complexity, influence without ego.
- Proven strengths in agility, change leadership, and proactive problem solving.
- Adept at leading strategically across functions and developing high-performing teams, while also serving as a hands-on contributor who drives clarity and accelerates execution.
Preferred Skills:
- Familiarity with ERP and financial planning tools.
- MBA, CPA, or CFA is a plus.
Location:
This is a hybrid role located in our San Francisco office, working 3 days per week from the office.
Pay & Benefits:
The anticipated new hire base salary range for this full-time position is $220,000-$310,270 + 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 ourPrivacy 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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