First-party delivery fulfillment
The problem
Sellers wanted to offer delivery on their own sites, but could only do so by hacking Square Online’s shipping setup or using third-party services that charged high commissions.
They wanted to bring delivery in-house to protect their margins and own the customer relationship.
The opportunity
- Let sellers take delivery orders on their own site, using their own or third-party couriers
- Integrate delivery orders into Square Point of Sale, streamlining operations
- Negotiate direct partnerships with delivery services for better commissions
Research and scoping
Delivery was new territory for Square in 2019, so I started by understanding the landscape and what sellers would expect.
After thorough competitive research, I listed every possible piece of functionality, then narrowed it to a core set that balanced value against effort to build.
I presented the proposed scope to stakeholders across product, engineering, business development, and support, and it was unanimously accepted.
Design explorations
Square Online already supported pickup orders, which had similar setup requirements, so I explored how delivery and pickup setup could coexist.
I explored multiple approaches, ranging from a simple addition to the existing structure to a full setup wizard.
After feedback from the design team and my PM, we committed to the wizard, and I built a higher-fidelity prototype to test.
Prototype testing
We tested the setup flow with Square sellers who’d shown interest in delivery. I wrote the interview guide and ran the sessions myself.
The flow was easy for sellers to navigate, and testers surfaced a few useful refinements. Confident in the approach, I moved on to fleshing out every flow.
Full designs
We also needed to design the downstream effects on sellers’ published sites and checkout, so I flew to New York for a week to work with the Buyer Experience team’s designer.
Together we designed the end-to-end experience, covering:
- Seller set up
- How buyers place a delivery order
- How sellers receive and fulfill it
- Communication between buyer and seller
We presented the full journey to Square Online’s leadership to a positive reception, and began preparing the hand-off to engineering.
But then… COVID-19
By the time designs were done and engineering was ready to build, it was March 2020. In-person shopping and dining ended almost overnight, and delivery became existential for sellers.
The comprehensively designed feature we’d spent a month finalizing could now make or break sellers’ businesses. There was no time to waste.
I went back to the drawing board for a true minimum viable product—something engineers could ship in weeks, not months, and designed to allow fast iteration.
We shipped it in three weeks and saw immediate adoption.
We kept shipping additional functionality almost weekly over the following months, working our way back to the comprehensive product we’d originally envisioned.
Within a month, Square Online had processed almost 3,000 delivery orders worth nearly $500,000, and continued to grow exponentially.
