Designing the Upgrade-to-Purchase Journey
Role: Defined problem space, facilitated cross-functional ideation, validated concepts through research, and shipped iterative experiments.
Team: 10 engineers & 1 PM
Outcomes: Created a north-star vision and turned it into roadmap-ready experiments, shipping 7 that led to 1,400+ new purchases and double-digit lifts across trials and paid feature usage.
Timeline: January 2025 - July 2025
Who are we designing for?
What problems were we trying to solve?
Customer problems:
It’s not clear what edition customers are on.
Admins are being jumped between tabs and out of context (e.g. In product > Admin Hub > Billing console).
Admins lack the info they need for informed decisions (differences between plans and their value), forcing them to waste time searching in WAC or other sources for pricing and feature details.
Business problem:
Due to the inconsistent experiences in different products that don’t line up strategically:
There are inefficiencies for designers and engineers working on experiences that touch edition awareness (EA), causing tech and design debt.
We are not realizing the upgrades and purchases we could be due to these inefficiencies and experience problems.
Hypothesis:
Design spike
The goal of the spike was to define the ideal trial and buy journey across all editions, products, and trials. To work toward this goal, the design spike focused on three areas:
1.
Understand the current state of edition awareness and trials.
2.
Investigate how competitors handle trials, such as Monday, Microsoft, Figma, Adobe, etc.
3.
Bring together cross-functional teams to brainstorm and get alignment.
