How and When Headway Pays Providers (Payment Schedule Explained)

Last reviewed: October 30, 2026

One of Headway’s biggest selling points is predictable pay. Instead of waiting for each insurer to process claims, providers receive a combined payout on a fixed schedule. Here is exactly how it works, based on Headway’s Help Center.

The short answer

Headway pays providers twice a month: on the 15th and on the last day of the month.

• Sessions confirmed between the 1st and the 15th are paid on the last day of that month.
• Sessions confirmed between the 16th and the end of the month are paid on the 15th of the following month.

Note the word confirmed. A session only enters a payout once you confirm it in Sigmund with the CPT code, diagnosis code and note. Confirming late pushes your money to a later payout.

Example

• You see a client on March 10 and confirm the session the same day → paid on March 31.
• You see a client on March 14 but confirm on March 17 → paid on April 15.

Bank processing can add a few days after the payout date.

Setting up direct deposit

Before Headway can pay you, you must verify your identity and link a bank account:

1. In Sigmund go to Settings → Billing.
2. Connect your bank through Plaid, or choose “Link with account numbers” if your bank is not listed.
3. If you link manually, Headway sends two small test deposits (between $0.01 and $0.99) within 1–2 business days. Enter the three-letter code from the deposit description on the Billing page to verify.

Any pending payments arrive about 3–5 business days after you link your account. After that, payouts follow the regular schedule.

Payments are processed through Stripe, which occasionally asks you to re-verify. If a payout seems late, first check that your bank details still show as linked and verified in the Billing tab.

Tracking your money in Sigmund

The Payments tab has three views:

• Upcoming – sessions scheduled for the next payout
• Past – grouped by payout date; expand a payout to see each session
• Pending – late-cancellation and no-show fees that have not been collected yet

Cancellation fees and private pay

Late-cancellation fees, no-show fees and private-pay sessions are only paid out after Headway successfully collects the money from the client. A fee can sit in Pending if a charge is still processing or a previous attempt failed.

Payments while you wait for credentialing

Insurers can take time to add you to their roster after you are approved. Headway’s Help Center says you are paid for insurance sessions once you are on the insurer’s roster, and Insurance Status shows your estimated guaranteed-payment eligibility date. During this wait, clients still pay their own cost-share per session, billed the day after you confirm it.

Tax forms

Stripe requires you to sign a W-9 (or W-8 for non-US persons). Headway uses this with your banking and identity details to prepare your annual tax forms, which are sent during tax season. Keep your Billing details up to date so forms go to the right entity.

New LLC or EIN?

Stripe may reject an EIN and business-name combination if the LLC was formed in roughly the last three months. Headway says Stripe may allow a 2–3 month grace period if you provide Form SS-4 and the IRS EIN verification letter (147C), which you send to Headway to upload.

Why is my Headway payment late? Checklist

• Did you confirm the session before the cutoff (the 15th or month end)?
• Are your bank details still verified in Settings → Billing?
• Is the payment a cancellation or private-pay fee that has not been collected yet?
• Are you past your guaranteed-payment eligibility date for that insurer?
• Has it been a few business days since the payout date for your bank to process it?

If all of these check out, contact Headway support from inside Sigmund.

FAQ

Does Headway pay even if the insurer denies a claim?

Headway says it pays providers on schedule whether or not the insurer has reimbursed Headway, and absorbs the loss if a claim is denied. See how Headway makes money.

How much does Headway pay per session?

Rates vary by license type, insurance plan, location and service. Headway’s practice consultants can quote rates for your practice.

Do group practices get paid differently?

Group practices have their own payment setup. See Headway’s group practice payments article.

Sources: Getting paid, How does Headway make money.