Founder Playbook · Sub Club by RevenueCat
10 tactics from Brandon Gdor
Increasing Monetization with Targeted Upsells - Sub Club Podcast by Revenue Cat
Watch the full episode“The product really has to be solved in a problem first and so you can't bring monetization in if there isn't like value that the user is finding that they're willing to pay for... for folks who are struggling with monetization that really is genuinely like the first troubleshooting step.”
Solve the Problem First — Monetization Problems Are Usually Product Problems in Disguise
Before optimizing any monetization lever, verify you have genuine product-market fit. Brandon frames monetization struggles as often being upstream product problems — if users aren't finding value, no paywall or upsell mechanic will fix it. This reset is the diagnostic first step, not an afterthought.
“A big learning that we've had is that users didn't even realize that they were in the free experience and so sometimes you just need to make it really obvious that hey you're part of a free product here and here's kind of the value that you're missing behind the paywall.”
Many Free Users Don't Know They're on the Free Plan — Tell Them Explicitly
One of onX Maps' biggest conversion discoveries was that free users were unaware they were missing premium features — they assumed the app was just limited. Explicit in-app education about being on the free plan was the first monetization motion before any paywall optimization. Awareness is a prerequisite to conversion.
“Getting that freemium mix right is what can really drive a product forward so I think it's a kind of an under-experimented-with aspect of premium subscription apps is actually moving features in and out of that premium experience to figure out what's retaining people and what's actually driving monetization.”
Experiment With Moving Features In and Out of Premium — Most Apps Under-Test This Lever
Most teams treat the premium feature set as fixed. Brandon's team actively tests which features belong behind the paywall — moving them in and out to find what actually drives conversion versus what was assumed. This freemium-mix experimentation is one of the most impactful yet underused levers in subscription app monetization.
“Take premium for instance — how often are your free users actually seeing the paywall and what are the motions you can do to increase the paywall view rate as well as then setting up capability so that you can run a lot of experiments on that actual paywall.”
Paywall View Rate Is the Most Underrated Monetization Lever to Increase First
Before A/B testing paywall copy or pricing, the more impactful lever is simply getting more eligible free users to see the paywall at all. Brandon frames paywall view rate as the primary traffic metric to optimize — more eyeballs on the paywall multiplies the impact of every subsequent conversion experiment.
“If there's a really large TAM like Duolingo you can afford to have millions and millions of free users whereas for some of our products it's more niche and so specifically in Hunt it's much more of a trial strategy because that TAM isn't like everyone out trying to learn a new language.”
TAM Size Should Determine Whether You Run Freemium or Free Trial — Not Preference
The freemium vs. free trial decision should follow addressable market size. Large-TAM apps can afford a massive free base because even a small conversion percentage yields huge subscriber counts. Niche apps like onX Hunt cannot — the trial model concentrates monetization effort on the smaller pool of highly-qualified users.
“My advice for the app builders out there is like until you really have a clear user need around an additional tier — when is the opportunity to bring it — because by introducing it too early it introduces all sorts of complexity into the business and it ends up being more work than it's actually worth.”
Don't Add a Second Tier Until You Have a Clear User Need Driving It
Multi-tier pricing adds product, engineering, support, and paywall complexity. Brandon's rule: don't add a tier until you have direct user evidence of a specific unmet need that tier would address. Premature tiering fragments the message and creates decision paralysis at the paywall without lifting revenue.
“What really works well with the Hunt tiering package is that it's baked in a user problem around the access that you get across the country — premium one state, premium two-state, Elite all 50 states plus Canada. From the user's perspective it's really easy to grok the difference.”
Anchor Tier Differences on a Single Intuitive Dimension Users Instantly Understand
onX Hunt's three tiers are differentiated on a single geographic dimension: one state, two states, all states. Users immediately understand the value difference without reading feature lists. When tiers are anchored on a concept users already think in — not a basket of sliced features — the paywall choice becomes obvious and conversion improves.
“Our Elite price is $100 which is a lot to ask for in the App Store... but in the context of the user and what they're spending for their hobby — if you think about hunters spending thousands if not tens of thousands of dollars a year — and sometimes the deals you can get on these partners can make up the value of the app in a single purchase.”
Brand Partnerships Can Justify a $100 Subscription When Discount Value Exceeds the Price
onX's Elite tier at $100/year bundles partner discounts from outdoor brands like First Light. For passionate hobbyists whose total annual spend on the hobby dwarfs the subscription cost, a single partner discount can recoup the price entirely. Contextualizing price against total hobby spend — not against other apps — eliminates sticker shock.
“Another really critical part of this strategy is like the who and when — so who are the cohorts that you're targeting and being really thoughtful around the specific cohorts... and then the when and the context — did they recently interact with a particular feature, how long have they been with the product.”
Target Upsells by 'Who and When' — Cohort Plus Context Together Drive Conversion
Effective upsells require two inputs working together: the right audience cohort (who has shown signals of value, engagement, or need) and the right contextual moment (recently touched a gated feature, approaching a usage limit). Either alone produces mediocre results; combining them creates upsells that feel helpful rather than intrusive.
“All Trails does a really nice job where if you're a free user and you interact with the 3D part of their map now the paywall actually has this great highlight video of 3D — it's giving you the value prop of 3D — so it goes back to that end-to-end user experience, having that continuity through the entire upgrade.”
Mirror the Feature the User Just Touched on the Paywall — AllTrails' 3D Map Example
The paywall should reflect exactly what the user was doing when they hit the upgrade gate. If they tapped on a 3D map, show a 3D map video on the paywall. This contextual continuity — from feature interaction to upgrade prompt to paywall content — creates a coherent narrative that converts far better than a generic feature list.