Headway · Go-to-market · Mid · 45 to 60 minutes

How should Headway scale paid acquisition?

Headway is a mobile app that helps people learn the key ideas from nonfiction books in about 15 minutes. Answer this product management case and get it graded line by line against a weighted rubric.

Growth strategy
Monetization
Analytical thinking
Experiment design
Prioritization

The situation

The Head of Growth asks you, a PM working on acquisition and onboarding, to recommend how Headway should scale in a crowded book summary market where larger rivals already advertise heavily. The team believes paid digital acquisition could work, but there is debate about the right funnel: send ads straight to the app store and monetize in app, send users through a web onboarding and checkout flow before they install, or use a web landing page that warms users up before the app store. The stakes are high because privacy changes have made targeting and measurement harder, app store commissions reduce margin, and the company cannot afford a long payback cycle if it wants to keep reinvesting in growth. Assume the annual plan is about $90 in core markets, shorter plans also exist, and leadership wants a path that can scale beyond one narrow audience. Your job is to propose a go to market plan for the next quarter that balances conversion, unit economics, speed of cash recovery, and long term brand health.

What to produce

Write a 1 to 2 page go to market memo.

Your answer must

Recommend which acquisition and conversion journey Headway should prioritize first, app store direct, web onboarding to checkout, or web landing to app, and explain the trade offs.
Define the first session monetization approach, including subscription term, trial or no trial, and whether discounting should play a role.
Describe how you would segment audiences and tailor ad creatives using user interests, goals, or challenges from onboarding and related signals.
Include a simple unit economics view covering CAC, net revenue after platform fees where relevant, and expected payback, plus what ranges would make the plan viable or not.
Lay out an experiment plan with success metrics, guardrails, and the main risks or failure modes you would watch in the first 6 to 8 weeks.

Constraints

Stay within paid digital acquisition and the current app plus lightweight web flows, not a major new product build.
Do not assume precise user level targeting or attribution on iOS because privacy limits measurement.
The plan needs a path to fast cash recovery so the company can keep funding acquisition without a large financing event.
Keep the recommendation suitable for one quarter of execution by a mid sized product and growth team.

Format

Use sections for recommendation, rationale, economics, experiments, and risks.

How Headway actually played it

Analyses a paid ads loop in which upfront annual payments fund the next round of ads, with web onboarding to avoid store fees.

Upfront payments can fund ads
Use onboarding data to tailor ads
Paid loops tend to wear down

Built from How Headway Took Over the Microlearning Market in Just 3 Years by Kurtis Morrison.