Let's reimagine
back-to-school shopping
Every August, millions of parents receive a school supply list — by email, paper, or school app — and spend hours figuring out where to buy each item for the best price. They toggle between Amazon, Walmart, and Target tabs, lose track of what they've bought, and overspend out of sheer exhaustion.
As a designer, I saw an opportunity to own this moment end-to-end — not just as a price comparison tool, but as a full platform where every school list lives. The kind of experience that brings parents back every year, not just once.
"The problem wasn't that parents didn't want to save money. It's that comparing prices across three stores takes longer than just buying everything at Walmart and being done with it."
The design challenge: make comparison feel effortless enough that parents actually do it — and give them a reason to come back beyond saving a few dollars.
A platform, not
a price checker
Early competitive analysis revealed a significant gap. Google Shopping compares prices generically. Honey applies coupons passively. The Shop app tracks orders after purchase. But nothing owned the school list moment — from receipt to purchase to giving back.
The opportunity was to design around four distinct jobs parents needed done:
Compare instantly
Scan or upload a supply list, instantly compare prices across Amazon, Walmart, and Target — without opening three separate apps.
Track what's bought
Check items off as you go. Never accidentally buy a second box of crayons because you forgot you already ordered from Amazon.
Give back automatically
Every purchase through Cubby funds classrooms that need extra support — transparent, automatic, and tied to real impact.
Every list, all year
Not just back to school — sports lists, art class, science fair, teacher wishlists. Every list is a reason to open Cubby.
Validating before
building anything
Before writing a line of code or opening Figma, I designed a parent research survey and distributed it through local Facebook parent groups. Within hours of posting, 6 responses came in — every single parent rated Cubby a 5 out of 5 on likelihood to use. The data was immediate and clear.
One parent's open-ended response stopped me in my tracks:
"The struggle of the best find for my price point."
And they kept coming. Parents described driving to multiple stores, not knowing when sales would happen, getting lists too late, and not even knowing what half the items looked like. The problem was bigger than price comparison.
"Not knowing when stores will do their sales — tax free weekend is a joke. Teachers have odd requests that are sold out in minutes."
Five insights shaped every design decision that followed:
Price anxiety is the core emotion — not convenience
Parents aren't just busy — they're stressed about cost. Real responses said it plainly: "The struggle of the best find for my price point" and "I always want the cheapest so I'm constantly comparing and will go to multiple stores to get the best deals." The real job isn't saving time. It's relieving financial anxiety.
Parents have no store loyalty — they just want the best price
Most parents said they shop "whoever" or a "mix" of stores. Nobody is loyal to one retailer for school supplies. That's exactly the behavior Cubby is designed to unlock — effortless comparison without the tab switching or driving to multiple stores.
The list itself is confusing — not just the shopping
One parent said: "I don't know what a chair organizer looks like — I need to do research or ask." This revealed an unexpected opportunity: Cubby can help parents understand what they're buying, not just where to buy it cheapest. Product education is a feature.
Timing and stock are just as painful as price
"Not knowing when stores will do their sales — tax free weekend is a joke. Teachers have odd requests that are sold out in minutes." Parents need sale alerts and low-stock warnings, not just price comparison. And they want the list earlier — ideally mid to late June — before stores sell out.
The need goes beyond school supplies
Parents unprompted asked for printer paper, sanitizer wipes, and other non-school items — noting they're cheaper at Sam's Club or HEB generic. Cubby has an opportunity to expand beyond the supply list into the full back-to-school shopping run.
Every decision
earns its place
Research consistently pushed against my initial assumptions. Each tradeoff below was informed by what parents actually told me — not what I thought they needed.
| Decision | Rationale |
|---|---|
| Image upload over live camera | Parents screenshot lists digitally — live scanning added friction for the most common use case. Upload first, camera as a secondary option. |
| Fully free, no premium tier | A paywall reduces sharing and makes school adoption harder. Affiliate revenue and brand sponsorships monetize the back end instead — without asking parents to pay. |
| Specific donation, not generic giving | Research showed vague "we give back" messaging didn't resonate. Tying donations to named classrooms in need created an emotional hook that drove sharing behavior. |
| Platform positioning, not price tool | "Every school list lives here" creates year-round retention. A price comparison tool gets used once in August. A platform gets returned to every season. |
| Schools as primary distribution | Consumer acquisition is expensive. School partnerships are a force multiplier — one relationship unlocks hundreds of families and gives Cubby institutional credibility. |
What guided
every decision
Speed is the product
If comparing prices takes longer than just going to one store, parents won't bother. Every screen asks: can this step be eliminated, automated, or collapsed?
Validate before you build
A research form before a single wireframe. Five parent conversations before a component library. The clearest design decisions came from listening, not assumptions.
Giving back is a feature, not a footnote
The donation mechanic isn't a marketing line — it's a core interaction that drives sharing, loyalty, and school adoption. It deserves visibility throughout the experience.
Design for return visits, not just first use
The goal is an app parents open every time a list hits their inbox — not just once in August. Platform thinking over tool thinking at every decision point.