AI TRAINING
Square AI Tools for Retail and Cafe Owners
Master Square's built-in AI features to save time, boost sales, and reduce stockouts.
What it covers
This hands-on workshop walks small retail and cafe owner-operators through Square's native AI capabilities, including Square Assistant, AI-generated item descriptions, automated email marketing, and sales-trend analysis. Participants leave knowing how to activate and configure each feature, interpret reorder suggestions, and run targeted promotions without needing a marketing team. The session is delivered as a half-day live workshop with screen-share walkthroughs and real account practice. No technical background is required — just an active Square account.
What you'll be able to do
- Activate Square Assistant and use it to handle common operational queries without staff involvement
- Generate, review, and publish AI-written item descriptions directly in the Square dashboard
- Create and schedule an AI-suggested email marketing campaign targeting lapsed customers
- Interpret Square's sales-trend graphs and identify which products to reorder or discontinue
- Configure low-stock alerts and act on automatic reorder suggestions to avoid stockouts
Topics covered
- Activating and using Square Assistant for daily operations
- Generating and editing AI-powered item descriptions
- Setting up AI-driven email marketing campaigns in Square
- Reading sales-trend reports and acting on insights
- Configuring automatic reorder suggestions for inventory
- Personalising promotions using purchase history data
- Understanding what Square AI can and cannot do
Delivery
Delivered as a half-day live session, either in-person at the venue or via video call with screen sharing. Each participant works on their own Square account throughout. Materials include a step-by-step PDF guide, a cheat sheet for Square AI shortcuts, and a 30-day action checklist. Hands-on exercises make up roughly 60% of the session. A short Q&A slot at the end addresses shop-specific questions.
What makes it work
- Designating one person (even part-time) to check AI suggestions and act on them weekly
- Customising AI-generated content before publishing to maintain consistent brand tone
- Running a small pilot email campaign first to test open rates before sending to the full list
- Revisiting Square's trend dashboard monthly and linking findings to buying or staffing decisions
Common mistakes
- Enabling Square AI features but never reviewing the suggestions, leading to ignored reorder alerts
- Publishing AI-generated item descriptions without editing for brand voice or local context
- Sending email campaigns to the full customer list instead of segmenting by purchase behaviour
- Confusing Square's trend summaries with full business analytics and making decisions on incomplete data
When NOT to take this
A retail group with multiple locations, a dedicated marketing manager, and a separate ERP system — they have outgrown Square's native AI and need integration-level training, not a Square-specific workshop.
Providers to consider
Sources
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