People upgraded when the message lived inside the feature they wanted to use.
A work management software company needed revenue quickly before its IPO. I designed upsell and plan migration flows that explain a locked feature in seconds and let people close the message and keep working, and upgrades to the Business plan tripled in the first week.
Client
A work management software company
I changed names and details to respect my nondisclosure agreements.
My role
Product design manager
Focus
Upsell, pricing, and plan migration flows
Result
Business plan upgrades tripled in the first week
The company needed revenue fast, and its customers needed to keep working.
In 2017, the company was preparing to go public and needed to grow revenue quickly. As product design manager, I led product design for the revenue team. We had three jobs: help people discover new features, move customers up to current plans, and retire outdated account types.
Everyone at the table knew the risk. People ignore an upgrade prompt that looks like a banner ad, and they get angry at one that blocks their work. The product also carried a long list of legacy user types, so a free collaborator, a licensed user, and a system administrator each needed a different, honest next step.
I started with interviews with the CEO, the CFO, and leaders in product, engineering, and marketing, then ran a design thinking workshop to agree on goals. We left with four rules. Keep people happy. Make the upsell look like the app, never like an ad. Drive upgrades for the people who find value in a feature. Let everyone else get back to work quickly. The first rule sat at the top of every review in five words: do not annoy users.
I put the message inside the feature, so the upgrade felt like the customer's own idea.
Feature announcements that look like ads get skipped. People engage with a feature when they feel they are inside it. So when a customer on a free or lower plan opens the Activity Log, the panel that shows who viewed a sheet and what changed, the panel opens like the real feature.
A short note explains why the feature is locked and which plans include it. A preview shows what the log would tell them. Close sits right beside Upgrade, with the same weight. I gave every step a time budget and tested the design against those budgets.
- Within 3 seconds, the person knows the feature is locked and why.
- Within 5 more seconds, the person sees what the feature is worth and chooses Show more.
- In under 30 seconds on Show more, the person understands the feature, their current plan, and how to upgrade.
- The person chooses Upgrade or closes the panel and keeps working.
Forty people tested the flow, and the prototype changed after every round.
I paired remote testing with the RITE method, short for rapid iterative testing and evaluation. We fixed problems between rounds instead of filing them for later. Click or tap a card to turn it over.
From the finance side
This is the right kind of tension to design in order to increase revenue.
Chief financial officerThe company
Click a locked feature and decide for yourself.
This prototype rebuilds the 2017 flow with sample data in a current, modern style under the Haven Works name. You are a free user working in a project sheet.
Things to try
- Open the menu on the Status column and point at Lock column to see the gentle hover tip.
- Click Lock column to pin the tip open with an Upgrade now button.
- Open the Activity Log from the right-hand toolbar, then choose Show more.
- Choose Upgrade, pick a plan, and finish the short checkout, which takes no real payment.
- Choose Close at any point to go back to your sheet.
The upsell borrowed the app's own colors, type, and parts, so the upsell never read as an ad.
I rebuilt the flow in a current work management style for this page. Every piece in the upgrade path comes from the same kit as the sheet itself, which is why the message feels like part of the product.
Color
- Haven navy
#0F1E3DThe top bar with the Haven Works wordmark and the left navigation rail - Action blue
#0068D9Share, Choose Business, Purchase, and focus rings - Upgrade violet
#6B3FD4The small gem that marks a paid feature, plus Upgrade buttons - Violet mist
#F1ECFCThe note that says which plans include a locked feature - Done green
#0E7A55Complete status pills, check marks, and the paid plan chip - Ink
#141A26Headings, body text, and confirmation toasts - Slate
#5A6378Secondary text, column icons, and timestamps - Canvas
#F5F7FAThe page behind the sheet and the pricing screen
Type
Wordmark
haven works
Inter
Page titles
Find the plan that fits your team
Inter
Sheet and panel headings
Product Launch Plan
Inter
Tip title
Upgrade to use
Inter
Body and menus
You're on the Free plan. Lock column comes with every paid plan.
Inter
Components
Upgrade gem, resting
A faint violet gem beside Lock column is the only sign of a paid feature, so a person who wants to sort rows sees nothing in the way.
Upgrade tip, hover
After a 200 millisecond pause on Lock column, the gem brightens and a tip explains why the feature is locked, so a passing cursor never sets off a pop-up.
Upgrade tip, click
A click pins the tip open with an Upgrade now button and a close button, because a click means the person wants the feature.
In-feature upsell panel
The Activity Log opens in its real side panel with a violet note, a one-line value statement, and Show more, with Close and Upgrade side by side at the same size.
Plan card
Each card shows the price, team size, and features in the same order, and the Activity Log line comes first so people can compare plans at a glance.
Checkout stepper
Three numbered steps, from choosing a plan to review and done, tell people exactly how much is left before they pay.
Principles
- I make the upsell look like the product, because people skip anything shaped like an ad.
- I put Close right beside Upgrade at the same size, so saying no takes one click.
- I explain why a feature is locked before I ask anyone to pay.
- I let the strength of the message follow the person's interest, from a faint gem to a pinned tip.
3x
upgrades to the Business plan from lower plans in the first week after launch
40
people tested across four rounds of RITE testing
$150M
IPO, about ten months after these designs launched
Upgrades to the Business plan tripled in the first week.
The winning patterns launched in 2017. The company went public about ten months later, and these flows were part of the revenue story behind its $150 million IPO. Click or tap a card to turn it over.
There is plenty more where this came from.
Names, brands, and data in my case studies are changed to protect my clients.
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