Vice President of Strategic Finance, Headspace Health

• 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

Desirable

• 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