How to Increase Monetization with Targeted Upsells — Brandon Gador, onX Maps

After learning that many users did not realize they were in the free experience, make it very obvious ('you're part of a free product tier, and here's the value you're missing behind the paywall'), even if it is somewhat disruptive. Also add education inside individual features explaining the outcomes users get by upgrading. Watch guardrail metrics so pushing harder doesn't drive people away: repeat usage, uninstalls, customer support tickets and App Store reviews.

Rather than fixing the paid basket up front, experiment with feature access over time to find which feature or user outcome most drives upgrades. Guest cites Headspace's journey of changing free access as a model.

Hunt's tiers map to a real user problem, access across the country: Premium covers one state, a Premium two-state package covers two, and Elite ($100) covers all 50 states plus Canada and Mexico, each with different durations. Shown at onboarding/paywall so users can grasp the difference immediately, unlike tiers sliced as arbitrary feature baskets. Guest advises not adding a second tier until there is a clear user need, since extra tiers add business complexity.

To justify the $100 Elite price, round out the tier with brand partnerships: Elite members get a discount or extra value from outdoor partners. Because hunting is an expensive hobby, a single partner purchase can pay back the app's cost. Partners such as outdoor apparel company First Lite also cross-promote onX, and being shown next to a premier brand builds association.

A horizontal growth team sets the model per app. Hunt (most mature, strong brand, niche TAM, seasonal use tied to hunting seasons) runs a trial strategy; newer Backcountry faces freemium competitors like AllTrails and Strava with more casual repeat use. Large-TAM apps such as Duolingo can afford millions of free users; niche ones can't. The chosen model decides which metrics the team optimizes.

Build the upgrade CTA into the natural user flow rather than a jarring interruption. Target on both who (specific cohorts) and when/context (recently used a related feature, time with the product). Carry the same value message through the paywall once the upgrade path starts. Also work to raise how often free users see the paywall and build capacity to run many paywall experiments.

When a free AllTrails user interacts with the 3D part of the map, the paywall that opens leads with a highlight video of the 3D feature, so the value prop matches what they just tried and the upgrade feels continuous.