Jobber
2026
Plus plan trial
A Plus free trial that starts the moment a feature would actually help, so the upgrade comes from experience, not a sales pitch.
Overview
The Challenge
Plus 2.0 relaunched Plus as Jobber's top-tier plan but customers were not seeing the value. Upgrades were stalling and contraction was high, largely because Plus read as a big team plan that growing businesses assumed was more than they needed. Telling them was not working, so the bet was to let them feel it through a free trial.
How customers used to find the trial
My role
Designing the trial experience
Product designer on the expansion trial, owning the design of the trial's entry points and the in-trial experience, inside a cross-functional team with a PM, engineering and data.
Research
What earlier trials had already taught us
Jobber had run expansion trials for years and the same pattern showed up every time. Customers upgrade when they feel the value, not when they are told. Give them a way to experience Plus and the decision makes itself.
“Plus is expensive and I don't know if it's worth the money. But if it has the features I need, I'm willing to upgrade.”
Service provider
“A few trial customers converted to Plus after feeling the time savings firsthand. Existing customers wanted the same but had no way to try it.”
Product, internal note
The insight
Customers upgrade when they feel the value, not when they are told about it. Give them a way to experience Plus and the decision makes itself.
The core idea
The trial starts at the exact moment a Plus feature would help, when someone mentions a teammate, checks profit on a job or hits a file limit, instead of on a generic upgrade page.
Design decisions and trade-offs
A trial that fits into real work
Start modal that matches the moment: The invite adapts to the entry point so the pitch reflects the exact feature they were reaching for.
In-trial status card: Shows days left, points to new Plus features and offers a path to an account manager, present without nagging.
A conversion moment at the end: As the trial winds down, a clear upgrade prompt turns it into a decision.
Low friction to start: Opt-in, no credit card, 14 days, desktop and mobile web.
Trying to @mention a teammate brings up the trial right where you'd use the feature
Looking for a client's files and photos brings up the trial right where they would live
Learn More shows what you are trialing and lets you upgrade in a tap, with eligible promotions surfaced right there
Results
A fast start and a clear signal on where value lands
The trial launched in August 2026 and beat its first-month goal of 500 trials well ahead of schedule. The most telling part was the spread: in-context moments like mentioning a teammate drove the most starts, while generic upgrade pages barely moved, which is shaping where to invest next. Conversion to paid is still too early to read, so I framed the launch to learn from placement first.
