Opening major-retailer access without requiring a subscription
Role
I led the design of the OnDemand purchase flow, defined how the service fee and optional subscription would appear, and translated eligibility rules into checkout behavior.
Impact
~670K shoppers placed their first Sezzle order through OnDemand.
Nearly 1 in 4 new U.S. shoppers · Oct 2024–Oct 2026
Timeline
12 weeks · U.S. launch in October 2024
Team
Partnered with product managers and engineers from four teams: Subscriptions, Orders & Issuing, Checkout, and Marketplace.
01 · The access barrier
Shoppers could browse major retailers, but buying required a subscription.
Survey feedback showed that some shoppers were unwilling to subscribe for a single purchase. OnDemand gave eligible shoppers another way to buy: pay a service fee per order. My design challenge was to keep that path clear while giving shoppers enough information to decide whether to join Anywhere.
Product response
Give eligible non-subscribers a pay a service fee for each purchase without committing to a subscription.
My design problem
Make subscription optional without making it invisible, and without letting the upsell interfere with purchase.
OnDemand removed the access barrier. But making subscription optional created the next design challenge.
Where should subscription live without becoming another barrier?
02 · The checkout trade-off
Balancing checkout completion with subscription conversion.
Making subscription optional created a new challenge: keep purchasing straightforward while giving users a clear reason to upgrade to Anywhere.
Technical constraint: Checkout depended on amount submission
Submitting the order amount triggered payment eligibility and checkout. The existing flow required users who subscribed first to return to amount entry before continuing, adding steps before purchase completion.
Checkout wanted to preserve the shortest path to loan review. I compared four directions based on when shoppers saw the offer, how much context they had before committing, and how many steps each option added.
Direction 1: Direct checkout opt-in
Banner click opens checkout with subscription selected.
Skips the separate subscription flow to keep users moving toward checkout.
Limited context before confirming a recurring membership during loan review.
Direction 2: Opt-in with Learn more
Users can explore benefits before continuing to checkout.
Optional benefits explanation before checkout, without a separate enrollment flow.
Users still confirm subscription alongside purchase and repayment terms.
Direction 3: Checkout-only upsell
Subscription is introduced on the loan-review screen.
Preserves the existing purchase flow, as recommended by Checkout.
A later offer risks lower visibility and subscription conversion.
Direction 4: Dedicated subscription flow (Selected and refined)
Users subscribe in a dedicated flow, then return to amount entry to start checkout.
Gives benefits and the recurring commitment their own space before joining.
Preserves the existing checkout logic.
Returning to amount entry adds steps and risks purchase drop-off.
03 · Iteration · Final decision
Keep the dedicated subscription flow and connect it directly to checkout.
I recommended keeping subscription benefits and the recurring commitment separate from loan review. Leadership aligned on this direction, and to address Checkout’s concern about added friction, engineering changed the backend logic so users could proceed directly to checkout after subscribing, without returning to amount entry.
03 · Scaling the experience
Eligibility rules determined what shoppers saw at checkout.
Product defined the eligibility rules. I mapped those rules and merchant capabilities to the payment methods, fee messages, and subscription offers shoppers would see. That gave engineering a reference for which screens to reuse and where the flow needed to change.
04 · OnDemand across the app
From finding a retailer to managing an order
OnDemand extended beyond checkout. Shoppers started in Shop, followed the purchase flow available for their retailer, and could manage virtual cards and review order details after purchase.
Main On Demand checkout, where Anywhere-eligible shoppers join Anywhere to unlock a multi-use virtual card.
Shopping in the Shop tab, where each merchant type gets its own checkout method.
From left to right: virtual card with a service fee, virtual card with no fee, gift card, and direct integration with in-store or online.
Virtual Card tab: manage active cards and find a store to create a new one
Orders tab: see the fees, payment schedule and virtual card behind each order.
Reflection
What I’d do earlier next time
Define decision criteria earlier
We kept returning to the same trade-off: how to keep checkout moving while giving shoppers enough context to decide whether to subscribe. I’d agree on those criteria with Product and Checkout before comparing designs.
Model the states before variants multiply
Mapping eligibility and retailer rules made it clearer which screens we could reuse and where the experience needed to differ. I’d build that map before designing individual flows.