Will the emails sound like collections-agency boilerplate?

No — that's the point. She references the specific invoice + PO + the work delivered, uses your voice, and stays warm at tier 1-2. Tier 3+ gets firmer but still professional ("I want to make sure we resolve this — can you confirm a payment date this week?"). Customers don't realize it's automated until tier 3.

Can she auto-send anything without my sign-off?

Only if you opt in for tier 1 (the lightest nudge). Tier 2+ requires your sign-off because the escalation tone matters and you may know context Tycoon Agent doesn't ("we just signed an expansion, don't push them this week"). Tier 4 always requires your call — Tycoon Agent never suspends service or writes off without you.

What if a customer disputes the invoice?

She flags it to you immediately with the dispute reason, the original PO, and the delivered work. She drafts a reply but doesn't send — disputes are too high-stakes for autopilot. Most disputes resolve at the invoice-line-item level once you provide context.

How does she handle customers who never reply?

After tier 3 with no response in 7 days, she escalates to your decision. Default options: (1) suspend service Friday + final demand, (2) hand to a collections service like CollBox, (3) write off. She tracks recovery rates by tier so you can see whether tier-4 escalation is worth the relationship cost.

Ask Tycoon Agent: Chase outstanding invoices

You'd think AR follow-up needs an ops hire — Tycoon Agent runs the dunning sequence with the right escalation tone for each customer.

The short answer

Tycoon Agent chases outstanding invoices by running a structured dunning sequence tuned to each customer's history. She pulls every unpaid invoice from Stripe and QuickBooks, sorts by days-overdue and dollar amount, and matches each to a tier: 1-7 days overdue = friendly nudge from your inbox ("hey just bumping this up — let me know if anything looks wrong"), 8-21 days = direct ask with payment link ("can you confirm a payment date?"), 22-45 days = escalation to the customer's billing contact + your CC, 46+ days = escalation flag for your decision (collections, suspend service, or write off). She drafts every email in your voice, sends after your sign-off (or auto-sends for tier-1 if you allow), and tracks responses. Output: a weekly Lark digest of AR aging, total outstanding, top 5 names, and what got collected vs escalated last week.

How Tycoon Agent actually does it

Pull AR aging
All unpaid invoices from Stripe + QuickBooks, sorted by days-overdue, total outstanding, top 10 by amount.
StripeQuickBooks
Match each to a tier
1-7d = friendly. 8-21d = direct ask. 22-45d = billing-contact escalation. 46+d = your decision.
Notion
Draft personalized emails
From your inbox, in your voice, referencing the specific PO/invoice number, with Stripe payment link inline. Different copy per tier.
GmailStripe
Send + track responses
Auto-send tier 1 if allowed, sign-off needed for 2+. Track replies, payment confirmations, partial pays.
GmailStripe
Weekly Lark digest
Total AR, total collected this week, top 5 oldest, escalation flags needing your call (suspend service / write off).
Lark

What it looks like in chat

YouChase all our outstanding invoices.

Tycoon Agent**AR snapshot:** $187,420 outstanding across 23 invoices. **Tier 1 (1-7d, $48k, 8 invoices):** Friendly nudges drafted. Auto-send if you allow tier-1? **Tier 2 (8-21d, $62k, 9 invoices):** Direct asks with payment links. Sign-off needed. **Tier 3 (22-45d, $51k, 4 invoices):** • Acme Corp ($23k, 38 days). Escalating to their AP@. Their last 3 invoices paid net-31 — likely just slow process. • Mercury Labs ($14k, 41 days). Last response: "sorry will pay next week" 12 days ago. Escalating to CEO + AP. • 2 more drafted. **Tier 4 (46+d, $26k, 2 invoices) — your call:** • Globex ($18k, 67 days). 3 unanswered emails. Recommend: suspend service Friday + final demand letter. • Initech ($8k, 89 days). They went quiet after Series B failed. Recommend: write off, mark uncollectible. First Lark digest: every Monday. Want me to send tier 1+2 after sign-off?

What you get back

Personalized dunning emails sent from your inbox at 4 escalation tiers, plus a weekly Lark digest of AR aging, total collected, and any invoices needing your decision (suspend service or write off).

Cadence: Daily review of new overdue, weekly Monday digest, on-demand escalation.

Chase outstanding invoices