Principal Product Manager, Subscriptions & Monetization Remote NY; Remote - Se

Principal Product Manager, Subscriptions & Monetization

About the Principal Product Manager, Subscriptions & Monetization at Headspace:

We are seeking a highly strategic and experienced Principal Product Manager, Subscriptions & Monetization to drive Headspace’s global subscription, pricing, and revenue strategy across all platforms (web, mobile, and partner channels). This Principal PM will be responsible for defining, building, and optimizing the product experience around how members discover, purchase, and manage their Headspace subscription. You will be the product leader who unlocks significant revenue growth and LTV (Lifetime Value) by defining new monetization strategies, improving our payment customer experience, and strategically packaging our offerings.

This role requires a unique blend of product management excellence, deep analytical skills, and a strong commercial acumen to drive the financial health and growth of the business. At Headspace, product leaders are expected to model experimentation with purpose, share feedback with care, and a deep commitment to the member journey.

What you will do:

As a Principal Product Manager, Subscriptions & Monetization
, you will be responsible for a variety of tasks crucial to the success of the Headspace Product team. Your day‑to‑day responsibilities will include:

• Monetization Strategy & Vision: 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.
• Pricing & Experimentation: 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.
• Payment Customer Experience (CX): 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.
• Subscription Offerings & Packaging: Define and launch new subscription tiers, packaged offerings, and bundles that align with customer value and Headspace's overall go‑to‑market strategy.
• Technical Product Ownership: 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.
• General Manager Mindset: 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.
• Cross‑Functional
  
  Collaboration:
  
  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.

What you will bring
:

To excel in this role, you should possess a strong foundation in both technical and commercial skills related to subscription models.

Required Skills:

• 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

Skills:

• 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).

Location: We…