Problem
At Square, only sellers on the e-commerce vertical had access to advanced shipping options. Retail and Invoice sellers were working around the gap. And inside Square Online itself, the experience was painful. The page reloaded with every change. Buying a single label took longer than it should have. The product question was how we can move it out of the silo, and improve the overall experience.
My role
Product design lead on the core shipping and label purchase flow. The team was a well-resourced, well-gelled cross-functional group: two PMs, a tech lead, two engineering managers, backend and frontend engineers, and two designers.
Three decisions that shaped the work
Align Shipping Manager with Order Manager
Order Manager was the most logical place for a seller to find shipping options. The problem wasn't a product problem, it was an organizational one: Orders and Fulfillment lived in different orgs and were each building their own version of the same idea. I made the case to both teams to align. In return we get, consistency for sellers, modernization for the platform, less duplicate work across orgs.
A faster purchase flow
The biggest pain point sellers brought up in interviews was the page reload on every change. I redesigned the flow around what actually had to happen, not what the page was technically doing. Package details loaded first, then rates and carrier options appeared once those inputs were in place. The sequencing grouped the requests into a single network call and selection got dramatically faster.
A smoother setup.
The design system pattern for setup flows bounced sellers back to the settings page after each completed step. It worked, but it made setup feel longer than it was. I broke from the pattern and designed onboarding as a wizard. A deliberate deviation from the design system, based on how sellers actually think about setup: as one continuous task, not a sequence of disconnected ones.
Outcome
It launched on my first year.
Adoption
80%
of shipment actions performed in Shipping Manager within 30 days.
Average sales
14.6
labels per seller, per month across Retail and Online
Reach
50%+
of new users were Retail sellers on the free plan
Monthly unique actions
Near-zero to 70k+
Click volume across year one