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$$$ Auto-invoice · Auto-remind · Auto-collect

Retainer Billing & Failed-Payment Recovery
that collects while you sleep

Stripe quietly fails 6–10% of recurring charges. The retainer-billing flow catches them automatically with a 4-stage recovery — typically recovers 78% of silent failures.

3 day
First overdue reminder
78%
On-time payment
$28K
Avg auto-collected / mo
Invoice
#INV-2026-0418
Due
May 22, 2026
To: Sarah Johnson · johnson@email.com
Initial consultation (1.5 hr)$525
Demand letter drafting$1,200
Medical records retrieval$425
Court filing + fees$2,100
Total Due $4,250.00
PAID ✓
Receipt sent · Stripe
3day
Overdue reminder cascade
Auto-fires at 9 AM
78%
On-time payment
↑ from 42% baseline
$28K
Monthly auto-collected
Avg firm, 4 coaches
0
Staff hours / invoice
↓ from 18 min each

This is the boring feature that pays for the snapshot in week one for most practices. Stripe silently fails 6–10% of recurring charges. If your stack doesn’t surface them, you keep delivering work for free until you happen to look at your MRR dashboard months later.

The 4-stage recovery flow

When Stripe reports a failed charge:

Stage 1 — Smart retry (Day 0). Stripe retries the charge at 4 hours. About 25–30% of failures resolve here with zero customer touch.

Stage 2 — Friendly nudge (Day 1). Email + SMS to the client in your voice, with a mobile-friendly self-serve payment-update link. Another 40–50% resolve here.

Stage 3 — Direct follow-up (Day 4). Same channels, slightly firmer. “If something’s changed with your situation, just reply and we’ll figure it out.” Another 10–15% resolve here.

Stage 4 — Manual escalation (Day 7). Slack ping to you with the client name, amount, and a one-click “send personal note” template. By this point ~85% of recoverable failures have resolved automatically.

Three properties matter:

  1. Works on mobile without login — Stripe’s hosted payment-update page does this
  2. Updates only the payment method — not “log in to the customer portal and find your way to billing”
  3. Confirmation back to both sides — client gets instant confirmation, you get a Slack ping

Get those right and recovery rate is 75–85%. Get any of them wrong and recovery drops to 30%.

What this earns the snapshot back

The math, conservatively:

  • 10 monthly retainer clients at $3,500/mo = $35K MRR
  • Industry-average involuntary churn rate: ~7% = roughly 0.7 failed charges/month
  • Average undetected duration before recovery flow: 60–90 days
  • Average loss per silent failure pre-recovery: $7,000–$10,500
  • Recovery rate with the flow: ~78%

Most practices recover one or more silent failures inside the first 30 days of installing the snapshot. That alone covers the $997 several times over.

What this looks like for the client

Done well, the client experience is better than what most practices have today:

  • They get a clear, friendly heads-up that their card needs attention
  • The update takes 30 seconds on their phone
  • No interruption to the coaching work
  • No awkward “your card declined” conversation

About 22% of failed payments turn out to be clients who would have ghosted anyway. The flow catches them while you can still have a real conversation about what changed.

Read the full case study → · Get the snapshot →

Invoice lifecycle

From generated to paid — touch-free

Five stages. Each one fully automated. You only see the money hit the trust account.

1
Generate
Timer entries + flat fees + expenses roll into a draft invoice. Branded with your firm logo, signature block, and trust-account language. One click to send.
2
Send
Email + SMS delivery with a "Pay Now" button. Stripe, LawPay, or PayPal — client picks. Payment link expires after 30 days; auto-regenerates on reminder.
3
Remind
Day-3 nudge, day-7 second reminder, day-14 firm follow-up, day-21 coach CC. Each escalates tone. Stops the moment payment clears.
4
Paid
Stripe webhook fires. Invoice marked paid in CRM. Pipeline advances. Trust-account split logged for IOLTA compliance. Slack pings billing.
5
Receipt
PDF receipt emailed within 60 seconds. Auto-filed to client folder. Thank-you SMS with optional review request after 48 hours.
Reminder cascade

The 4-message rhythm that gets you paid

Same tone you'd use yourself — calibrated by day, firm-branded, signed by an coach name.

Day 0 · Invoice
$
Hi Sarah — your invoice #INV-2026-0418 for $4,250 is ready. Pay securely: [link]. Due May 22.
Day 3 · Friendly
$
Just a heads-up — invoice #INV-2026-0418 is due in 4 days. Quick to pay: [link]. Reply if anything's unclear.
Day 7 · Second
$
Hi Sarah, invoice #INV-2026-0418 is now 2 days past due. Need a payment plan? Just reply. Otherwise: [link]
Day 14 · Firm
$
Sarah — invoice #INV-2026-0418 is 9 days overdue. To keep your file active, please pay by Friday: [link]. — Michael, Partner
Pre-wired processors

Plug into the rails you already trust

Trust-account compliance built in. IOLTA splits handled. No reconciliation gymnastics.

💳 Stripe 🏡 LawPay 🅿️ PayPal 🏦 IOLTA-ready 📊 QuickBooks sync 🧾 Clio import 🏧 ACH bank transfer 💵 1099 export
Stop chasing payment

Auto-Invoice Your Firm — Live in 24 Hours

Included in the $997 Coaching Snapshot. Stripe / LawPay / PayPal pre-wired. IOLTA-compliant. 10 dedicated config hours.

Book Demo Get Snapshot