How to Cross-Sell on Squarespace: Strategies That Actually Work
Cross-selling on Squarespace requires a fundamentally different approach than most ecommerce guides suggest. Those guides are written for Shopify, where upsell apps are abundant and highly mature. On Squarespace, the tooling is different, the customer experience expectations are different, and the strategies that work reflect that.
Here's what actually works for cross-selling on Squarespace — based on the mechanics of the platform and what converts in practice.
Understand What Cross-Selling Is (and Isn't)
A cross-sell is a suggestion for a complementary product — something that adds to what the customer already intends to buy, rather than replacing it. The goal is to increase the order value by making a relevant, timely suggestion the customer genuinely considers.
What it isn't: a random product recommendation, a catalog dump, or a pushy pop-up that interrupts the buying flow. The best cross-sells feel like helpful advice from someone who knows the products well.
The Squarespace Context
Squarespace stores tend to have strong visual identities and curated catalogs. The customers who shop there expect a considered, aesthetic experience. This matters for cross-selling: the offer needs to feel native to the store, not bolted on.
This means your cross-sell widget design matters almost as much as the product suggestion itself. A poorly styled offer on a beautifully designed Squarespace store will actually hurt conversion — because it breaks the trust the store design has built.
Strategy 1: Start With Your Natural Pairs
Every catalog has natural product pairs — items that logically belong together. A candle and a holder. A shirt and a belt. A ceramic mug and a pour-over dripper. These are your highest-probability cross-sells because the complementary relationship is obvious and the customer is already halfway to making the connection.
Start there. Create one cross-sell offer per natural pair. Measure for two weeks. These will outperform everything else in your first month.
Strategy 2: Use Data for Non-Obvious Pairs
Beyond the obvious pairs, your order history often contains surprises. Products that sell together frequently but that you never would have paired intentionally. UpsellGrow's Frequently Bought Together feature surfaces these automatically — analysing your Squarespace order history and showing you the actual co-purchase patterns in your store.
Some of your best cross-sell opportunities are hiding in your order data right now. You just haven't looked.
Strategy 3: Match the Moment to the Offer Type
Not all cross-sells work equally well at all stages of the buying journey. Here's a rough guide:
Product page — below Add to Cart: Works for single-product cross-sells. The customer is evaluating — show them something that adds to what they're considering.
Product page popup (fires on ATC click): Works for higher-AOV suggestions or bundles. The customer has committed to buying — they're receptive to one more thing before they move on.
Slide-out cart: Works well for last-chance cross-sells. "Before you checkout, did you see this?" One suggestion, high relevance, low friction.
Cart page: Works for bundle suggestions. The customer can see their whole order — a bundle offer makes the value proposition ("add this and save") easy to evaluate.
Strategy 4: Keep It to One Suggestion
The most common mistake in cross-selling is showing too many options. Three to five products in a cross-sell widget looks like a catalog section, not a recommendation. One or two suggestions that are genuinely relevant outperform five mediocre ones every time.
Focus creates urgency. A single, specific suggestion — "customers who bought this also bought that" — is more compelling than "here are five things you might like."
Strategy 5: Exclude What's Already in the Cart
Nothing undermines a cross-sell faster than suggesting a product the customer already has. UpsellGrow's condition builder lets you add a "product exclusion" rule — hide the cross-sell if the suggested product is already in the customer's cart. This is a simple rule that significantly improves the relevance of your offers.
Implementing Cross-Sells on Squarespace
UpsellGrow handles all of this natively on Squarespace 7.1. Install the plugin, create a cross-sell offer, select your trigger and suggested products, choose the position, add any conditions, and publish. The whole process takes under ten minutes for your first offer.
Ready to Start Earning More From Every Order?
UpsellGrow adds upsells, cross-sells, bundles, and frequently bought together offers to your Squarespace store — across 5 pages and 19 positions. No coding. Setup takes minutes.