Basket & Checkout Redesign

Context

Thortful’s core value proposition goes beyond buying a single card and sending it to a single address. From early on, the business was built around gifting at scale: buying multiple cards in one order and sending them to different people, at different addresses, often for different occasions and delivery dates.

When I joined Thortful, the company was growing quickly, moving from selling very few cards to handling a much higher volume of orders. As this growth accelerated, new customer behaviours began to emerge. Although the existing basket and checkout had been designed to support multi-card and multi-address gifting, it became clear that users were struggling with specific steps in the journey as order complexity increased.

These issues surfaced most clearly through Customer Support. Customers regularly became confused when managing multiple recipients, different delivery addresses, and delivery dates. Calendars, address assignment, and understanding which card was going to which recipient were frequent points of friction. Although the overall experience appeared functional on the surface, users repeatedly got stuck at the same moments in the basket and checkout flow.

The basket quickly became one of the most critical parts of the product. Even when the rest of the app experience worked well, users were unable to complete their purchase if this part of the journey broke down. For an e-commerce business built around complex gifting scenarios, this was a significant risk to conversion, customer trust, and the ability to scale the product offering over time.

Why this was challenging

Designing this basket and checkout experience was fundamentally different from a standard e-commerce flow. Most checkouts are built around a simple mental model: one order, one delivery address, one delivery date. Thortful’s gifting model broke that assumption from the start.

A single order could contain multiple cards, each intended for a different recipient, sent to different addresses and often scheduled for different delivery dates. This meant that key delivery steps were not linear. Address selection, delivery dates and confirmations repeated per card, creating a highly dynamic journey that was easy for users to lose track of.

As order complexity increased, users frequently struggled to understand which card was going to which person, on what date, and to which address. Small moments of uncertainty quickly compounded into confusion, especially when managing several cards at once. The risk was not just friction, but users abandoning the flow entirely because they no longer felt confident about what they were about to send.

From a business perspective, this complexity had a direct impact. Customer Support volumes increased significantly around multi-card and multi-address purchases, and small errors in the basket created costly operational issues downstream. At the same time, the business needed a solution that did not limit flexibility, as gifting multiple cards to multiple people was a core part of Thortful’s value proposition and future growth.

The challenge was clear: design a checkout system capable of handling a highly complex set of delivery scenarios, while making the experience feel simple, predictable and safe for users. Reducing cognitive load without removing flexibility became the central design problem to solve.

What we heard from users

As order complexity increased, the same issues began surfacing repeatedly through Customer Support tickets and direct conversations with customers.

People were not struggling with buying a card. They were struggling with managing who each card was for, where it was going, and when it would arrive once multiple recipients were involved.

Customer Support consistently highlighted recurring problems such as:

• Users losing track of which card was assigned to which recipient

• Confusion around delivery addresses when sending multiple cards in a single order

• Uncertainty about delivery dates, especially when cards were meant to arrive on different occasions

• Mistakes that only became apparent after checkout, leading to cancellations, refunds, or manual intervention from Customer Support

To understand these issues more deeply, I worked closely with the Customer Support team while also running user testing and observational research. I invited customers into the office and sat next to them as they completed real purchase sessions, observing how they managed complex orders involving multiple cards, recipients, and delivery dates.

Even confident users hesitated, backtracked, and second guessed themselves when assigning addresses and delivery dates. The mental effort required to keep track of several cards at once was simply too high.

Another recurring source of confusion was delivery timing. Depending on weekends or postal cut offs, some cards were intentionally delivered earlier than the actual occasion. To support this, the product included a “Don’t open until” label, allowing recipients to understand when a card was meant to be opened.

In practice, many users either missed this option or were unsure when to apply it. As a result, cards sometimes arrived earlier than expected without clear guidance, creating awkward experiences for recipients and frustration for senders. This issue appeared frequently in Customer Support conversations and highlighted how easily delivery intent could be lost during checkout.

A key insight emerged quickly: the problem was not a lack of flexibility, but a lack of clarity and reassurance.

Users needed to feel confident that every card was going to the right person, at the right address, on the right date, without having to hold all that information in their head at once.

This made it clear that improving the basket and checkout experience was not about adding more options, but about reducing cognitive load and making the journey feel predictable, transparent, and safe, even in the most complex gifting scenarios.