Head of Subscriptions & Monetization

About the role
The owner of Pocket's consumer subscription business across our hardware device and mobile and desktop apps. Your job is to grow subscription revenue by improving conversion, monetization and retention.

Pocket has already reached hundreds of thousands of customers and is scaling toward millions. Every one of them buys a device, sets it up and starts using our mobile and desktop apps. Pocket Pro, our subscription, is a core part of the business and one of our biggest growth levers. You will own its P&L end to end, from the first paywall to renewal.

You will set the subscription and monetization strategy, define how we measure it, run a relentless experimentation program and work directly with engineering and design to ship improvements. You should be equally comfortable setting revenue targets with founders, designing a pricing test and digging into cohort data yourself.

You'll work side by side with our Head of Growth & Marketing, who owns customer acquisition and device sales. They bring users in, and you turn them into active, paying, long-term subscribers. On the product side, you'll work closely with our CTO to prioritize and ship subscription improvements. You'll report directly to the founders.

This is a senior, hands-on role. At first you'll be designing and shipping experiments yourself. As the business scales, you'll build and lead the subscriptions and monetization team.

What you'll own

• Pocket's subscription P&L and revenue targets

• Conversion: onboarding, paywalls, trials, checkout and Free → Paid across mobile, desktop and our Shopify store

• Monetization: pricing, packaging, monthly vs annual, plan structure, credits, upsells and new paid features

• Retention: activation, engagement, churn, cancellation and save flows, win-backs

• Involuntary churn: failed payments, dunning, billing recovery and renewal flows

• Lifecycle: push, email, in-app messaging, trial reminders and renewal communications

• Experimentation: relentless A/B testing across every part of the subscription funnel, with clear hypotheses, prioritization and rollout

• Analytics: cohort retention, LTV, attach rate, trial conversion, involuntary churn and revenue per user, plus a clear view of where subscription revenue is leaking and how to fix it

• Product: working directly with engineering and design to ship subscription improvements fast

• Shopify subscription attach together with our Head of Growth & Marketing: post-purchase upsells, thank-you page offers, device + Pro bundles

• Building and leading the subscriptions and monetization team as Pocket grows

What we're looking for

• 7+ years in consumer subscription, growth or monetization, including 3+ years owning subscription revenue or a subscription P&L

• A track record of growing subscription revenue at scale in consumer apps, with quantified results on conversion, ARPU, retention and churn

• Experience in consumer subscription apps, ideally hardware + subscription (e.g. Oura, Whoop, Peloton, Eight Sleep, Garmin) or strong subscription apps (e.g. Calm, Headspace, Duolingo, Strava, Noom, Flo)

• Deep expertise in pricing and packaging: monthly vs annual, plan tiers, trials, credits and paid feature launches

• Strong experimentation skills: test design, sample sizing, reading results and knowing when a result is real

• Hands-on with paywall and subscription tools (RevenueCat, Superwall), product analytics (Amplitude, Mixpanel) and lifecycle tools (Braze, Customer.io )

• Strong analytical skills: you can pull and read the data yourself and build the business case for where to invest

• Strong product and commercial judgment: you optimize for long-term subscription revenue, not short-term conversion at the cost of churn

• Willingness to be hands-on now while building a team over time

• Clear communication skills and the ability to influence founders, engineering and cross-functional stakeholders

• High ownership, low ego, intellectual honesty, and the ability to execute without constant direction

• Shopify / e-commerce CRO experience is a strong plus

• Experience building a subscription or monetization function from early stage is a strong plus

What we offer

• Ownership of the subscription business at a rapidly scaling consumer hardware and software company

• Direct access to founders and significant influence on company and product strategy

• High autonomy and the ability to ship your ideas quickly and see the impact in revenue

• A large, fast-growing user base across the US and Europe, so experiments reach significance fast

• The opportunity to build Pocket's subscriptions and monetization team as we grow from hundreds of thousands to millions of customers

• Base salary of 170,000–210,000, depending on experience

• Meaningful equity through Pocket's employee stock option plan

About the interview

• Quick intro call (15 min): experience, motivation, compensation expectations and location fit

• Deep dive into a subscription business you owned: revenue, key levers and the experiments that moved it

• Subscription case study based on a realistic Pocket funnel and P&L problem

• Cross-functional interview with Growth & Marketing and Engineering

• Interview with the founders

• Reference check

• Offer

• Onboarding

About Pocket
Pocket is a Y Combinator W26 company building a premium hardware plus software product in the AI voice recorder space. We are obsessed with quality and speed. We are scaling very fast in the US and European markets and building a device experience that can become the category leader.