Checkride

Setting up payouts via Stripe Connect

Connect your school's bank account, pay instructors, and read settlement reports.

Checkride uses Stripe Connect to handle the money side of training: collecting from students, paying CFIs, and reconciling everything against lesson records. You connect once, then payouts run on a schedule you control.

What gets paid out

When a lesson is completed and signed off:

  1. The student's recorded payment method is charged for the lesson amount (Hobbs/Tach time × the aircraft's hourly rate, plus the CFI's instructional rate).
  2. A platform fee is deducted.
  3. The CFI's share (configured per CFI on their profile) is held in a Stripe Connect account.
  4. On the next settlement run, the held balance pays out to the CFI's bank account.

One-time school setup

  1. Settings → Payouts → Connect.
  2. You'll be redirected to Stripe to verify your school's legal entity (name, EIN/SSN, address, owner identity).
  3. Stripe returns you to Checkride once verification is in progress. Most schools clear within an hour; some take 1–2 business days.
  4. Until verification clears, your school's payout status shows as pending and the Settle now button is disabled.

Per-instructor setup

Each CFI must also connect their own Stripe Connect account — that's the bank account their share lands in. See the CFI-side flow at Connecting your payout account. The school owner can see at a glance which CFIs are missing payout setup from the Payouts → Roster view.

Until both the school AND the receiving CFI have payouts set up, lesson payments stay in Checkride's holding account. CFIs see a "Payouts setup needed" banner on their dashboard.

Reading a settlement report

Payouts → Settlements lists every settlement run, with a downloadable CSV per run. Each row includes:

  • Lesson date, CFI, student, aircraft (if any)
  • Gross amount charged to the student
  • Platform fee, CFI share
  • Resulting payout reference (matches the Stripe transfer ID)

If a payout fails (e.g., closed bank account), the CFI receives a notification and the row is flagged for retry. Payouts can be retried up to three times before they're moved to manual reconciliation.

Cancelling a settlement

A settlement that hasn't yet posted to Stripe can be cancelled from its detail view. Once a transfer has been initiated with Stripe, the only path is a reversal — contact support.

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Still stuck?

Email support@trycheckride.com and reference this article. We'll get back to you with steps for your specific setup.