Headspace · 2 weeks ago
Principal Product Manager, Subscriptions & Monetization
San Francisco, CA
Full-time
Hybrid
Lead/Staff
$162K/yr - $259K/yr
8+ years expHeadspace is a company dedicated to providing mental health support through innovative technology and evidence-based content. They are seeking a Principal Product Manager, Subscriptions & Monetization to drive the global subscription and revenue strategy, focusing on optimizing the product experience for members and enhancing monetization strategies.
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No H1B
Responsibilities
Define the multi-year product vision, strategy, and roadmap for Headspace’s core monetization streams, including subscription packaging, paywalls, and feature differentiation to maximize revenue and user retention
Lead the strategy, design, and execution of pricing and promotional experiments (A/B testing) to optimize conversion rates and average revenue per user (ARPU) across different customer segments and markets
Own and optimize the end-to-end payment and billing experience (including checkout flows, recurring billing, dunning, and alternative payment methods) to reduce involuntary churn and minimize transactional friction
Define and launch new subscription tiers, packaged offerings, and bundles that align with customer value and Headspace's overall go-to-market strategy
Work closely with Engineering to define and prioritize requirements for the core subscription platform, billing systems, and APIs that ensure security, scalability, and financial accuracy
Establish and rigorously track key business and product/business metrics (e.g., Conversion Rate, ARPU, Churn Rate, LTV) and use data modeling to forecast financial impact and inform strategic product decisions
Serve as the primary product partner for Core Experience Product, Finance, Legal, Data Science, and Marketing teams to ensure alignment on monetization goals, revenue targets, and go-to-market plans
Qualification
Required
8+ years of experience in Product Management, with at least 2+ years focused specifically on subscription models, monetization, pricing, or billing platforms
Proven track record of defining and launching successful products that directly contributed to revenue growth and/or improved customer Lifetime Value (LTV)
Exceptional strategic thinking and analytical skills, capable of translating complex business problems and financial goals into clear product roadmaps and specifications
Deep understanding of subscription economics and hands-on experience with A/B testing and experimentation for monetization features
Strong communication and interpersonal skills, with the ability to influence and align stakeholders at all levels
Preferred
Experience with global payment systems, billing systems (e.g., Zuora, Recurly, Stripe), and related financial compliance
Experience in the digital health, wellness, or consumer subscription SaaS sectors
Familiarity with multiple monetization models (e.g., freemium, tiered subscriptions, usage-based pricing)
Benefits
Equity
Comprehensive healthcare coverage
Monthly wellness stipend
Retirement savings match
Lifetime Headspace membership
Generous parental leave
Company
Headspace
Headspace is a mental health company offering AI companionship, coaching, therapy, psychiatry, and mindfulness tools for everyday support.
501-1000 employees
Funding
Current Stage
Late StageTotal Funding
$320.85MKey Investors
Oxford Finance LLCBliscePacific Western Bank
2023-07-26Debt Financing· $105M
2022-02-14Series C
2021-10-31Secondary Market
Leadership Team
Tom Pickett
Chief Executive Officer
Andy Puddicombe
Co-Founder
Recent News
2026-01-09
2026-01-08
Company data provided by crunchbase