Director, Finance

Summary

Join Headspace as the Director of Finance for our B2B business, leading financial strategy, forecasting, and planning. You will partner with cross-functional leaders, translating business priorities into actionable financial plans. This role requires a strong analytical background and experience as a strategic business partner. The ideal candidate has high-tech industry experience and thrives in a fast-paced environment. You will manage a team, develop scalable planning processes, and drive strategic initiatives. The position offers competitive pay and benefits, including equity and a comprehensive healthcare package.

Requirements

• 10+ years of progressive finance experience, with a focus on business partnership, strategic planning, and performance optimization, ideally within a B2B or enterprise SaaS environment
• At least 3-5 years of people management experience
• Proven success supporting or leading finance for a B2B business unit or commercial organization
• Ability to influence all levels of leadership to drive actions, behaviors, decisions and business outcomes
• Ability to lead teams to deliver exceptional results and drive business growth
• Exceptional track record of self-motivation, prioritization, initiative, and integrity
• Strong written and oral communication skills with experience in presenting to business partners with confidence, conviction, and credibility
• Advanced experience with Excel and PowerPoint applications

Responsibilities

• Primary finance lead for our Employer (B2B) business, shaping long-term growth strategies by aligning business priorities with resource planning, revenue modeling, and performance insights
• A trusted advisor to the Finance Leadership team and business stakeholders, proactively highlighting risk and opportunities related to business growth and optimal investment decisions or outcomes and providing business modeling and what-if scenarios specific to the Employer channel
• Lead the development of scalable planning processes for the B2B function, including quarterly and annual budget cycles, forecast accuracy, and performance management practices
• Drive strategic planning initiatives including market expansion, pricing strategy, and ROI analysis of new GTM investments
• Support pricing and negotiation of employer and partnership deals
• Support Sales & GTM strategy through rep-level productivity modeling, LTV/CAC analysis, and funnel conversion insights to optimize customer acquisition and retention
• Lead, coach, and develop finance team members, while serving as a cross-functional thought partner and change agent across the organization
• Business Partnership with clear, impactful financial insights and strategic recommendations to senior non‑finance audiences, including executive leadership and Board materials when required
• Partner with Sales, Partnerships, Client Success, Product, Marketing, and Data teams to drive alignment on commercial strategy, resource deployment, and performance optimization — translating financial data into executive-level decisions

Preferred Qualifications

• Ideally will have experience in both private and public companies
• Familiarity with tools and processes used in go-to-market planning, enterprise sales forecasting, or customer segmentation
• MBA / CPA / CFA designation preferred but not required
• Experience with EPM (e.g. Adaptive Insights) systems a plus
• Experience with Tableau a plus

Benefits

• Comprehensive healthcare coverage
• Monthly wellness stipend
• Retirement savings match
• Lifetime Headspace membership
• Generous parental leave