Connect Outlook and
Square with AI

Automate the flow between your communication hub and point-of-sale system. Stop manually forwarding payment receipts, copying customer details between systems, or compiling sales reports from email threads.

No code required
Live in minutes
SOC 2 Type II

What you can automate today

Redbird gives your team ready-to-run workflows — just connect your accounts and go.

Send Outlook emails when high-value Square transactions are completed

Automatically notify account managers via Outlook when a Square transaction exceeds a threshold amount. Include customer details, payment method, and product information so your team can follow up with personalized service or thank-you notes.

Create Square invoices from Outlook email requests and send confirmation

Parse invoice requests sent to a shared Outlook inbox, generate corresponding Square invoices with line items and customer data, then reply with the invoice link. Eliminates manual data entry between email communication and billing.

Archive Square daily sales summaries to Outlook-connected SharePoint folders

Automatically pull end-of-day sales reports from Square and route them to designated SharePoint folders organized by location and date. Email summaries to relevant stakeholders with key metrics highlighted in the message body.

Sync Square customer profiles when new contacts are added to Outlook

When sales team members add new contacts to Outlook with specific tags or custom fields, automatically create or update matching customer profiles in Square with contact details, notes, and communication preferences.

Send weekly Square revenue reports to distribution lists via Outlook

Generate formatted weekly revenue reports from Square data segmented by location, payment type, and product category. Automatically send to department-specific Outlook distribution lists with visual summaries and trend analysis.

Enrich Outlook contacts with Square purchase history and transaction data

When viewing a contact in Outlook, automatically surface their complete Square transaction history, average order value, and last purchase date. Gives sales and support teams instant context without switching between systems.

Live in four steps

No engineers, no pipelines to maintain. Redbird handles the connectivity — you focus on the outcome.

01

Connect your accounts

Authorize Outlook and Square with OAuth or API credentials. Redbird never stores your data — it just passes through.

02

Describe what you want

Tell Redbird what to do in plain language — no SQL, no code, no configuration files required.

03

Review and activate

Redbird shows you exactly what it will do before running anything. Approve the workflow, set a schedule, and switch it on.

04

Let it run — and iterate

Workflows run on your schedule or on triggers. Every run is logged. Adjust with natural language at any time.

Built for data-driven teams

Redbird understands both Microsoft 365's communication schemas and Square's commerce data structures, so you can automate workflows between email, calendar, and payment operations without custom development.

AI that speaks both Outlook and Square

Redbird maps Outlook's Exchange message formats, contact fields, and calendar events to Square's transaction objects, customer profiles, and inventory items. Parse payment confirmations from email bodies, match customer records across systems using fuzzy logic, and transform Square's JSON payment data into readable email summaries. The platform handles timezone conversions between calendar events and transaction timestamps, maps custom fields between contact records and customer profiles, and intelligently routes notifications based on location, product category, or transaction attributes.

Email body parsing
Contact-to-customer matching
Transaction formatting
Location-based routing
10×

faster than exporting Square CSVs and emailing them manually

No spreadsheet exports, email attachments, or manual recipient lists required

Auto-generated reports

Redbird can pull from Outlook and Square simultaneously, merge the results, and format a polished report — sent on a schedule or on demand.

Trigger-based alerts

Set conditions in natural language. Get notified in Slack or email the moment a threshold is crossed in either Outlook or Square.

Enterprise-grade security

SOC 2 Type II certified. Data flows encrypted in transit and at rest. Fine-grained permission controls with full audit logs.

Bidirectional sync

Push data from Outlook into Square, or from Square back into Outlook. Resolve conflicts with configurable merge rules.

Full audit trail

Every workflow run is logged — what ran, what changed, and why. Replay or revert any individual step at any time.

Triggers & actions for every team

Start automations from any Outlook email, calendar event, or Square transaction — then take action in either system.

Outlook
Triggers & Actions
Trigger

New email received

Trigger when an email arrives in a specific folder, from a specific sender, or matching subject line criteria.

Trigger

Calendar event created

Fire when a meeting is scheduled, updated, or includes specific attendees or keywords.

Trigger

Contact added or updated

Trigger when new contacts are created or existing contact fields are modified in Outlook.

Action

Send email

Compose and send emails from a designated account with dynamic content, attachments, and formatted HTML.

Action

Create calendar event

Schedule meetings with attendees, locations, and custom fields populated from external data.

Action

Update contact record

Add or modify contact fields, notes, and custom properties in Outlook contacts.

Square
Triggers & Actions
Trigger

Payment completed

Trigger when a transaction is processed successfully, with filters for amount, payment type, or location.

Trigger

Refund issued

Fire when a refund is processed, capturing the original transaction details and refund reason.

Trigger

Invoice sent or paid

Trigger when Square invoices are created, sent to customers, or marked as paid.

Action

Create invoice

Generate Square invoices with line items, customer information, and payment terms from external data.

Action

Update customer profile

Add or modify customer records in Square with contact details, notes, and preferences.

Action

Retrieve transaction history

Pull payment records, refunds, and order details for specific customers, dates, or locations.

Outlook
+
Square

Ready to connect your stack?

Join teams that have automated the connection between their communication platform and point-of-sale system. Build Outlook and Square workflows in minutes, not weeks.

Get started → Book a demo