Head of Subscriptions & Monetization

About Pocket

At Pocket, we’re building the future of human memory.

Some of the most valuable information in our lives disappears when a conversation ends: an idea, a decision, a detail we wish we could remember. Pocket helps us hold onto it.

We’ve built an AI-powered device that captures real-world conversations and turns them into searchable transcripts, summaries and next steps. Backed by Accel and Y Combinator (W26), we’ve already sold 500,000 devices.

Our ambition goes beyond recording. We believe the things you learn, discuss and experience can become useful context for the AI tools you already use, and for products that don’t exist yet.

About the Role

Buying a Pocket is the beginning of the customer relationship. Your job is to make Pocket Pro valuable enough that people choose it, keep using it and renew.

You’ll own our consumer subscription P&L, from the first paywall to renewal. You’ll set the strategy, inspect the cohort data and work with engineering and design to ship improvements. Growth & Marketing owns acquisition and device sales; you’ll work alongside that team and the CTO, reporting directly to the founders. This starts as a hands-on role, with the opportunity to build the function as the business grows.

What You’ll Own

• Subscription revenue targets, measurement and the priorities behind them.

• Conversion across onboarding, paywalls, trials, checkout and free-to-paid journeys on mobile, desktop and Shopify.

• Pricing, packaging, plans, credits, paid features, upsells and device-plus-Pro offers.

• Retention, lifecycle communication, cancellation flows, win-backs and recovery of failed payments.

• An experimentation program with clear hypotheses, reliable analysis and decisions about what to ship.

• Cohort retention, LTV, attach rate, trial conversion and revenue per user, with a clear view of what to improve next.

• Building and leading the subscriptions and monetization team over time.

What We’re Looking For

• Seven or more years in consumer subscriptions, growth or monetization, including at least three owning subscription revenue or a P&L.

• Quantified results improving conversion, revenue per user, retention and churn in consumer subscription apps.

• Practical depth in pricing, packaging and experimentation, including sample sizing and interpreting results.

• Hands-on experience with subscription, analytics and lifecycle tools such as RevenueCat, Superwall, Amplitude, Mixpanel, Braze or Customer.io.

• The ability to investigate data yourself, make a commercial case and work across founders, engineering and design.

• Judgment that favors durable customer value over a short-term conversion lift that creates churn later.

Bonus Points

Hardware-plus-subscription experience; Shopify or ecommerce conversion optimization; or building a monetization function from an early stage.

Why Join Pocket?

You’ll own a business line, not just a collection of tests. You’ll have direct founder access, an existing customer base and the chance to connect pricing and product decisions to measurable revenue outcomes. The role includes equity through Pocket’s employee stock option plan.

Interview Process

A 15-minute introductory call; a deep dive into a subscription business you owned; a Pocket-style funnel and P&L case; cross-functional conversations with Growth & Marketing and Engineering; a founder interview; and references. Successful candidates then move to offer and onboarding.