Head of Subscriptions & Monetization
About Pocket
Pocket builds a credit card sized AI device that captures real-world conversations (meetings, phone calls, field visits) and turns them into transcripts, summaries and action items. Customers buy the device on Pocket's Shopify store, then use the mobile and desktop apps. Revenue comes from both hardware and the Pocket Pro subscription.
Launched in October 2025
Reached a $27M annualized revenue run rate within about 5 months, growing around 50% month over month
Subscription revenue has since grown to roughly $20M ARR and recently doubled
Raised $11M led by Accel, with Y Combinator and angels including Guillermo Rauch (Vercel) and Mati Staniszewski (ElevenLabs)
Small, fast and international team, now raising its next round with top-tier VCs
Why this role exists
The device gets Pocket into people's lives, the subscription is what makes the business last. Most subscribers are on annual plans, so the first big renewal cycles are coming up, and there is clear room to improve activation, conversion and monthly churn. Pocket needs one person who lives and breathes subscription: where the paywall sits, what triggers after which action, where a referral loop belongs, and how to measure all of it.
This is the first hire fully dedicated to that, with a direct line to the founders and a big say in how the company grows.
What you'll own
Everything that happens after the device arrives, from first unboxing to renewal.
Metrics
Activation rate, time-to-first-value, trial start rate, trial-to-paid conversion, paid attach rate, annual plan mix, renewal rate, churn, retention and subscriber LTV.
Scope
Activation: device setup, account creation and getting new users to first value as fast as possible
Onboarding and paywalls: paywall placement and optimization across mobile and desktop, free vs. Pro tier design
Conversion: trial start rate and trial-to-paid conversion, annual plan adoption
Engagement and upsells: in-app upsells, referral loops, push notifications and lifecycle messaging
Retention: cancellation and save flows, renewal strategy, win-back
Pricing: pricing and offer testing
Experimentation: build and run a high-velocity program, shipping several meaningful experiments every month plus smaller iterations continuously
Not in scope
Customer acquisition and device sales sit with the Head of Growth & Marketing. You'll work closely with that team but your focus starts once the device is in the customer's hands.
How you'll work
Report directly to the founders
Partner with the CTO to prioritize and ship experiments across the mobile and desktop apps
Work side by side with the Head of Growth & Marketing (they bring users in, you turn them into active, paying, renewing subscribers)
Start as a hands-on, independent operator: you design your own mockups in Figma, set up your own tests and pull your own data
Build your own team over time, starting with a designer
What we're looking for
Must-haves
5+ years in consumer product, with hands-on ownership of subscription growth or monetization
Experience in a consumer subscription business, ideally hardware + subscription (e.g. Oura, Whoop, Eight Sleep, Garmin, Peloton) or strong mobile subscription apps (e.g. Calm, Duolingo, Strava, Noom, Flo)
Proven, quantified results on metrics like activation, trial start, trial-to-paid, ARPU, retention or churn
Obsessed with experimentation and A/B testing, with a track record of running tests end to end
Strong analytical skills: you read data and size opportunities yourself, without waiting on a data team
Thrive in a fast, high-intensity early-stage environment
Nice to have
Hardware experience, especially device activation and onboarding
Hands-on with tools like RevenueCat, Superwall, Amplitude, Mixpanel, Braze or
SQL
Desktop apps or multi-platform products
Shopify or e-commerce CRO experience
Probably not a fit if
Your background is mainly B2B or enterprise SaaS
You've been in strategy or people management only for the last few years and no longer run experiments yourself
You're looking for a structured, big-company setup with dedicated design and data support from day one
Who thrives at Pocket
Pocket is an intense place to work. The team is small, moves very fast and expects a lot of ownership. People who do well here are direct, hands-on, hungry to build something big, and genuinely enjoy being close to the numbers. In return you get real scope, a direct line to the founders and meaningful equity in a company that is growing very quickly.
Location and logistics
Office: 500 3rd St, San Francisco, CA 94107
Onsite: at least 2 out of every 3 months in SF, as key decisions are made in person
Relocation: supported, including for candidates moving from Europe
Visa: sponsorship and H-1B transfers available
Compensation
Base: $170K-$210K, with flexibility for an exceptional candidate
Equity: meaningful equity on top
Interview process
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
A question to think about
If you'd like to get ahead, have an answer ready for this one:
Tell us about a monetization experiment you ran: the metric before and after, why it worked, and what you learned if it did not.