Number of Seats/Users: Square Loyalty offers discounts based on the number of users or seats. A higher volume typically leads to a better discount structure, especially for enterprise-level usage.

Commitment to a Long-Term Contract: Discounts are often provided to companies that commit to using the service for a longer period (e.g., 1-year or 3-year contracts). A longer commitment shows Square Loyalty that the company is serious and willing to invest in the platform long-term.

No Active Discounts: Companies that are not already receiving other active discounts may have a better chance of qualifying for additional discounts from Square Loyalty. Square Loyalty reserves discounts for new customers or those not currently under promotional pricing.

Volume or Usage Commitment: Square Loyalty offers discounts if you agree to a minimum amount of usage or transaction volume. This could be based on data storage, transactions, or other metrics tied to how much you will use the platform.

Enterprise-Level Negotiation: Companies that qualify as “enterprise” due to their size or complexity (e.g., having large teams, multiple departments, or geographical presence) may be eligible for additional discounts from Square Loyalty. Such companies are often in a position to negotiate for better pricing.

Early Renewal or Prepayment: Square Loyalty often offers discounts if you renew early or prepay for the entire contract period. This is a common approach to securing a lower price.

Here at Spendbase our internal data shows that Square Loyalty is generally seen as a strong, low-friction way to boost repeat business, especially for teams already on Square POS. But there are clear cost and flexibility gaps that many Spendbase clients flag.

Key positives our clients highlight
– Seamless integration
– Works natively with Square POS and existing customer database.
– No extra hardware or apps; staff learn it quickly.

• Simple for end customers
• Phone-number based sign‑in at checkout.

• Automated point tracking and reward application, no punch cards.

• Real impact on repeat sales

• Some clients report more than half of sales tied to loyalty members.

• Easier upsell and targeted promos to top customers.

• Decent customization (within limits)

• Ability to choose between visits, spend, or points.
• Can configure tiers and basic promotional campaigns.

Main pain points we see
– Pricing and ROI
– Cost feels high to smaller merchants and those with many infrequent visitors.
– Usage-based pricing (by visits or active customers) makes budgeting harder.
– Some clients feel they pay for a large pool of sign‑ups who rarely return.

• Limited data capture and customization
• Inability to easily collect extra fields (email, birthday, preferences) at sign‑up.
• Phone/SMS-centric flows create issues in regions where text marketing is weaker or costly.
• Restrictions around excluding certain items (e.g., sale items) from redemptions.
• Messaging and branding of automated comms not flexible enough for some brands.

How we typically advise Spendbase clients
– Right-size the program:
– Align rewards with gross margin; avoid overly generous point values.
– Choose between visit-based vs spend-based earning using historical ticket size data.

• Control cost drivers:
• Regularly prune inactive loyalty members where possible.

• Monitor active-visit volume vs subscription band to prevent unnecessary overage.

• Maximize marketing value:

• Layer Square Loyalty with separate email tools if richer segmentation is needed.
• Use loyalty data to target top customers with higher-ROI discounts instead of broad promos.

Overall, our internal data shows Square Loyalty works best for businesses that value simplicity and tight POS integration over deep customization, and that actively manage reward economics to keep costs in line.