Behind the product

Built for Square operators who cannot wait for the end-of-day report.

Square Sidekick exists because the most important moments in a business often happen quietly: a discount is used, a high-value sale lands, a regular returns, stock drops, or a call goes unanswered.

Read the storySee the product

founder signal

built from Square operator experience

operator led
problemburied Square events
surfacecritical push alerts
contextcustomers / stock / tender
actionoperator knows now
Square Sidekick team security screen

founder note

Sidekick is built from the operator side of the counter.

Christian Ritter built Square Sidekick after years of living with the same gap many Square sellers feel: Square records the details, but operators still need a faster way to know what deserves attention.

The first product layer is the iOS app: real-time alerts, top customer intelligence, transaction detail, low-stock thresholds, sales goals, discounts, gift card activity, refunds, team protection, and location-aware Square settings.

The voice layer extends the same idea to phone operations. Calls, orders, transcripts, payment links, and escalations should become part of the same operating picture instead of living somewhere else.

principles

The product is designed around operational attention.

Sidekick should feel like a focused command system, not another place to dig.

Signal over noise

A notification should earn the interruption. Sidekick is built around the alerts a Square operator actually needs during the day.

Operator context

Sales, customers, inventory, discounts, refunds, gift cards, and team controls are connected so the detail does not live in separate silos.

Trust first

Square OAuth, location scope, sensitive controls, and permission refreshes are visible because operators need to trust the system.

trust model

Trust is part of the interface.

Operators should know which Square account is linked, which locations are in scope, and when sensitive data or controls are protected.

Square Sidekick Square settings screen

operator controls

Visible permissions. Clear scope.

Square OAuth connection path
Location selection and scope visibility
Manager PIN gates for sensitive controls
Push routing around operator preferences
Alert rules tuned around real business events

journey

From hidden activity to a cleaner operator system.

01

Square operator

The product starts with real operating pain.

Square has the data, but the most important signals can be buried while the floor is busy.

02

iOS alert layer

Critical events become push alerts.

Discounts, refunds, low stock, top customers, gift cards, goals, and transaction detail surface where operators already work.

03

Voice layer

Calls become part of the same system.

Voice AI adds phone orders, transcripts, payment links, and escalation paths into the broader Sidekick operating layer.

next step

See what Sidekick surfaces from Square.

Explore the product system or try the interactive demo to see how buried business activity becomes operator context.

Product systemLive demo