VP, Strategic Finance

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 ca