Connect Gainsight and
Square with AI

Sync payment activity, transaction data, and revenue trends from Square directly into Gainsight customer health scores and success workflows. Stop manually exporting Square reports to update account health, track expansion signals, or trigger renewal plays.

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.

Update customer health scores based on Square payment volume trends

Automatically pull Square transaction data and revenue trends into Gainsight health scorecards. When payment volume drops or refund rates spike, adjust health scores and trigger at-risk plays without manual data review.

Trigger expansion plays when Square revenue crosses usage thresholds

Monitor Square sales data for accounts hitting revenue milestones or expanding to multiple locations. Automatically create Gainsight success plays and CTAs when customers show growth signals worth an upsell conversation.

Alert CSMs when customer payment activity drops below baseline

Track Square transaction frequency and payment volume by customer account. When activity falls below historical averages for 30+ days, create high-priority Gainsight CTAs and notify the account owner immediately.

Enrich QBR decks with Square revenue and transaction analytics

Pull Square sales performance, payment trends, and location-level data into Gainsight QBR templates automatically. Build executive business reviews showing actual product usage, revenue growth, and seasonal patterns without manual report aggregation.

Create Square invoices when Gainsight renewal opportunities close

When renewal or expansion opportunities move to closed-won in Gainsight, automatically generate Square invoices with correct line items, payment terms, and customer details. Eliminate duplicate data entry between CS and finance workflows.

Sync Gainsight account segmentation to Square customer tags and metadata

Push Gainsight customer segments, lifecycle stage, and health status into Square customer profiles as tags and custom attributes. Enable sales teams to see CS context at point-of-sale and tailor interactions based on account health.

Live in four steps

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

01

Connect your accounts

Authorize Gainsight 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 AI understands both Gainsight's customer success data model and Square's payment and transaction schemas, so you can connect revenue activity to retention workflows without custom API work.

AI that speaks both customer success and payments

Redbird maps Square's transaction objects, payment methods, refund events, and location hierarchies to Gainsight's account structure, health scorecards, CTA types, and success plan frameworks. The platform recognizes when Square customer IDs need matching to Gainsight company records, translates payment volume into health metrics, and handles timezone and currency differences across both systems. No middleware or custom field mapping required.

Transaction → Health Score mapping
Customer ID reconciliation
Multi-location aggregation
Revenue trend calculation
10×

faster than exporting Square CSV reports and manually updating Gainsight scorecards

No spreadsheet downloads, VLOOKUP formulas, or weekly data reconciliation sessions

Auto-generated reports

Redbird can pull from Gainsight 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 Gainsight 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 Gainsight into Square, or from Square back into Gainsight. 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 customer success events in Gainsight or payment activity in Square, then take action across both platforms.

Gainsight
Triggers & Actions
Trigger

Health score changes

When a customer account's health score drops to yellow or red in Gainsight.

Trigger

Success plan milestone completed

When a customer completes or misses a success plan objective or milestone.

Trigger

Renewal opportunity stage updated

When a renewal or expansion opportunity moves to a new pipeline stage.

Action

Create or update CTA

Generate a call-to-action for the CSM with context and priority level.

Action

Update account health scorecard

Modify specific health score measures or overall account health status.

Action

Log timeline activity

Add an entry to the customer timeline with external system context.

Square
Triggers & Actions
Trigger

Payment processed

When Square completes a payment transaction for a customer account.

Trigger

Refund issued

When a refund is processed through Square for any transaction.

Trigger

Revenue threshold crossed

When cumulative payment volume for a customer crosses a defined dollar amount.

Action

Create invoice

Generate a new Square invoice with line items, customer details, and payment terms.

Action

Update customer profile

Modify Square customer record with tags, notes, or custom attribute values.

Action

Send payment link

Generate and send a Square payment link to a customer email address.

Gainsight
+
Square

Ready to connect your stack?

See how Redbird AI syncs Gainsight and Square in minutes. Stop copying payment data into health scores and start automating customer success workflows with real-time revenue intelligence.

Get started → Book a demo