Outsales
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Stripe
Integration · Revenue Signal

Outsales + Stripe

Your billing data, weaponized for AI sales

Outsales reads every Stripe event — trial starts, plan changes, churn risk, past due — and turns them into AI Worker triggers. Live MRR dashboard, automatic deal creation, churn prevention sequences.

What syncs

Two-way, real-time, transparent

Connect once. Outsales reads from Stripe and writes back to it — your data stays where you expect it, always.

  • Customers and subscriptions
  • Trial start / end events
  • Plan changes (upgrade / downgrade)
  • Invoices and past-due alerts
  • MRR / ARR calculations
  • Churn and reactivation events

Automate Stripe workflows with AI

Common workflows our customers automate when they connect Stripe.

✓

Trial expiration AI follow-ups

Day 12 of 14-day trial → Outsales drafts the upgrade nudge using account engagement context. Day 15 (expired) → reactivation sequence.

✓

Churn prevention sequences

Stripe signals churn risk (usage drop, cancellation flag) → Outsales triggers the Customer Success Worker with a save-the-deal email.

✓

Auto-create deals from new Stripe customers

New paying customer? Outsales creates a deal in your CRM, sets the right amount, opens an Onboarding Worker handoff.

✓

MRR + churn dashboard inline

Stripe MRR, active subs, trials, churned, past due — all live on the Outsales Dashboard. No tab-switching to billing tools.

✓

Past-due reactivation

Past-due invoice triggers an AI Worker that drafts a soft reactivation email using payment history context.

✓

Expansion signal detection

Plan upgrade in Stripe → flagged as expansion. AI Worker drafts a renewal-pricing conversation 30 days before next renewal.

What Stripe powers in Outsales

Connect Stripe and unlock these Outsales modules.

Autonomous CRM

Stripe MRR widget on the Dashboard. Active subscriptions inline on every contact. Live revenue at a glance.

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Buy Intent

Trial start, plan upgrade, churn signal — each feeds the intent score with weighted deltas.

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AI Follow-up

Trial expiring soon → AI Worker drafts upgrade email. Past-due payment → reactivation sequence. Churn signal → CS handoff.

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Connect Stripe in 2 minutes

No code. No SDK. Just OAuth.

  1. 1Click Connect Stripe in Outsales Settings → Integrations.
  2. 2Authorize via Stripe Connect — read-only by default, write access optional.
  3. 3Outsales runs initial backfill of customers, subscriptions, MRR.
  4. 4Stripe events stream in real-time from now on.
  5. 5MRR widget appears on Dashboard. Stripe subscriptions inline on contact view.