Jobber
2026
Seat & add-on purchasing
Decoupling the paid seat from the person, so Jobber customers can buy and manage users on their own.
Overview
The Challenge
Jobber's per-user pricing was quietly working against the business. Users were a plan differentiator so service providers chose between Core, Connect, Grow and Plus partly on team size rather than the features that fit them. Adding users was manual and one at a time, prices were hard-coded in a way that locked legacy-priced customers out of self-serve, and because the model was a flat price times quantity with no volume advantage, Sales and Success discounted by hand, creating irregular pricing and no enforced rules.
This was not only a UX problem. It was a hard prerequisite for Plus 2.0, a relaunch of Jobber's top-tier plan with new pricing, packaging and features, which set out to roughly double new Plus customers from around 1.4K to 3K. Until the per-user system was rebuilt, that launch could not move.
My role
Owning the design across three phases
Sole designer on the Growth team across this three-phase initiative. I owned design end to end: discovery, information architecture, the seat model, every purchase entry point and the manage and cancel flows. I partnered with my PM and the Subscription Infrastructure team who owned the billing backend, and worked across Monetization, Sales and Success, sequencing the whole system to land ahead of the Plus 2.0 date.
Research
Starting with the feedback we already had
Rather than run new interviews, I used the feedback the company had already collected. I combed Enterpret and Amplitude, our customer-feedback and product-analytics platforms, including transcripts of past Sales and Success calls, for how service providers manage their team: how often they add or remove people and why.
What we learned
The signal was consistent. Providers with fluctuating teams were constantly deactivating and reactivating staff just to manage cost, and several said they would happily buy several seats at a discount up front even if the seats sat empty for a while, because their headcount was always moving. Underneath the specific complaints was one cause: the paid seat was welded both to a specific person and to the plan itself, and that coupling was the source of the friction.
“I pay $40+ CAD per user/month, many are part-time and only work one day a week. Constantly deactivating and reactivating staff to manage costs is a lot. Would absolutely bulk-buy 5 or 10 seats even if not all are filled right away, because my team is always fluctuating.”
Carmen
Cleaning, ~17 users
“I pay $40+ CAD per user/month, many are part-time and only work one day a week. Constantly deactivating and reactivating staff to manage costs is a lot. Would absolutely bulk-buy 5 or 10 seats even if not all are filled right away, because my team is always fluctuating.”
Carmen
Cleaning, ~17 users
"I've already done the math. One add-on user costs almost the same as a plan that includes five, so I'm switching to the teams plan. I won't pre-buy seats but I'll move up a tier when the numbers make sense. For me it always comes down to cost."
Damian
E-commerce founder
The core idea
So the central move was to separate the paid seat from the person in it. Service providers could buy seats in bulk without assigning anyone yet, and deactivating a team member no longer cancelled their subscription, the seat stayed open for someone else. That one reframe unlocked self-serve bulk purchasing and cascaded into every downstream flow.
Design decisions and trade-offs
A clear model inside hard constraints
One model across all four entry points: The seat concept had to read consistently across the Plans page, Checkout, Manage Team and Account & Billing, so providers learned it once and it held everywhere.
Deactivate is not cancel: I redesigned the flow so freeing a seat could not be mistaken for cancelling the subscription, paired with deferred cancellation so a cancelled seat stayed usable until the end of the billing cycle.
Clarity as the differentiator: Benchmarking per-seat pricing across tools like Asana, Slack and Figma showed the advantage is a legible model, not a clever one. The billing platform also supported only fixed pricing with no true per-user price, so I designed for simple math that builds trust and seat changes that behave exactly as expected, without over-promising savings the system could not back.
Scalability vs speed: The initiative first scoped a fully scalable bulk-discount model, then cut it to protect the launch date. I re-scoped to ship the key price points and a clean seat model on time, and documented what a transparent bulk-pricing experience would need next.
Before & after
The rebuild is clearest in the purchase experience itself. The old flow added users one at a time and stopped providers cold at the plan limit. The new in-place modal lets them buy and manage multiple seats without leaving Manage Team and without tying a seat to a specific person.
Seat is not tied to a person
Freeing a seat keeps the subscription intact and the seat open for the next hire
The limit is a path, not a wall
Hitting the cap leads straight into buying more seats
Bulk in one action
Providers add multiple seats at once instead of repeating a one-user flow
Testing
I pressure-tested the design in two passes. First, quick and internal: I asked coworkers to complete the core tasks, buying seats in bulk and freeing a seat without cancelling, which surfaced small points of confusion I could fix before locking anything in. Then I built an unmoderated prototype test on Lyssna and set participants a realistic task to finish on their own. It validated the model, with most participants completing the task without help, so we moved into build confident the seat concept read clearly.
Final designs
One seat model, every entry point
The final redesign focused on improving clarity across everyday financial tasks through stronger hierarchy, simplified navigation, and more contextual transaction feedback. The updated interface made balances easier to compare, actions easier to locate, and activity flows easier to understand at a glance.
Assigning a team member to a seat
Results
Early impact
The system launched in July 2026. In the first month, of 7,361 service providers who saw the purchase prompt, 22% bought seats and under 3% cancelled one. Beyond adoption, the rebuild unblocked the Plus 2.0 launch it was a prerequisite for, and it removed the manual billing workarounds that internal teams had been absorbing.
