Jobber
2026
Plus plan trial
Designing a mobile experience that helps users discover new music, explore playlists, and connect with artists through a simple and engaging interface.
Overview
The Challenge
Plus 2.0 relaunched Plus as Jobber's top-tier plan, with a repackaged feature set and new multi-user pricing. The problem was that customers were not seeing that value. Upgrades into Plus were stalling and contraction was high, largely because Plus read as a big-team plan, so growing businesses assumed it was more than they needed. Telling them about the value was not working. The bet was to let them feel it directly through a free trial of Plus, so the decision came from experience instead of a sales pitch.
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 did not upgrade because someone described Plus to them. They upgraded once they had felt what it did for their own work. The ones who converted had used a Plus feature firsthand and the ones who stalled were being sold value they had never actually touched.
“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
Earlier trials had also taught us that placement decides everything. An invite buried in Settings went nowhere while one offered at the moment of need landed. So the trial was designed to begin at the exact in-product moments where a Plus feature would solve a problem the customer was having right then. Mentioning a teammate on a job, checking profit on a job, hitting a file limit: each became a natural, in-context door into the trial, instead of a generic upgrade page. I also worked toward one consistent in-trial experience so even a customer in more than one trial got coherent guidance rather than competing nudges.
Design decisions and trade-offs
A trial that fits into real work
In-context entry points across the journey: Rather than one upgrade page, the trial opens from the specific features that prove intent, from team mentions and profit alerts to files, revenue goals and the sales pipeline.
A start modal that matches the moment: The invitation adapts to the entry point it came from, so the pitch a customer sees reflects the exact feature they were reaching for, not a generic Plus ad.
An in-trial status card: A persistent card shows days left, points to the new Plus features to explore and offers a path to talk to an account manager, keeping the trial present without nagging.
A conversion moment at the end: As the trial winds down, a clear upgrade prompt turns the experience into a decision.
Low friction to start: Opt-in, no credit card, 14 days, on 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 surpassed its first month goal of 500 trials well ahead of schedule. Just as valuable as the volume was the spread: starts clustered around genuine in-context feature moments, with prompts like mentioning a teammate driving the most trials, while generic upgrade and add-on pages barely moved. That is directly shaping where to invest next. Conversion to paid is still too early to read since the first cohorts are only now finishing their trials, so I framed the launch to learn from placement performance first.
