You'd think this needs a contracts manager — Tycoon Agent scans every PDF, email, and QuickBooks invoice and tells you 90 days before each one auto-renews.
The short answer
Tycoon Agent scans every contract source weekly and flags expirations 90 days out. She pulls contract metadata from 4 sources: (1) QuickBooks vendor records with explicit term/renewal fields, (2) Notion contracts database if you maintain one, (3) Gmail search for 'contract', 'renewal', 'agreement', 'effective date' attachments parsed for dates, (4) DocuSign or PandaDoc completed envelopes with terms. She extracts vendor, monthly amount, end date, auto-renewal clause, and notice period. Anything expiring or auto-renewing in the next 90 days lands on the report. For each, she prepares a renegotiation packet: current spend, alternatives quoted (top 3 competitors with pricing), usage data showing if you're getting value, and a draft renegotiation email. Weekly Monday Lark report. Most teams cut 15-25% off vendor spend in year 1 just by renegotiating before auto-renewal locks them in for another year.
How Tycoon Agent actually does it
- Scan all contract sources
QuickBooks vendor records, Notion contracts database, Gmail search for contract attachments (parsed via OCR), DocuSign/PandaDoc envelopes. Build unified contract registry.
QuickBooksNotionGmailDocuSign
- Extract terms and dates
Per contract: vendor, monthly amount, term length, end date, auto-renewal clause, required notice period to terminate. Flag anything missing for manual review.
- Flag 90-day expirations
Anything ending or auto-renewing in 90 days = renewal window. Sort by dollar value × notice period urgency. Top of list: high-value contracts with short notice deadlines.
- Prepare renegotiation packet per contract
Current spend, alternatives (top 3 competitors with pricing pulled from G2/Capterra), your usage data showing value, draft renegotiation email asking for X% discount.
- Weekly report + calendar reminders
Monday Lark: contracts expiring next 90d, packet ready per contract. Google Calendar reminders 60d, 30d, 14d before each notice deadline.
LarkGoogle Calendar
What it looks like in chat
YouWhich contracts are expiring soon?
Tycoon Agent**6 contracts expiring or auto-renewing in next 90 days. Total annual value: $87,400.** **1. Datadog — $890/mo, $10,680/yr — auto-renews May 12 (notice deadline: April 28).** ⚠️ 2 days left. **Packet ready:** New Relic quoted $620/mo, your APM usage is below 40% of plan. Draft email asks for 25% discount or you switch. Reply 'send' to ship today. **2. HubSpot — $2,400/mo, $28,800/yr — auto-renews June 1 (notice deadline: May 1).** Packet ready: ActiveCampaign quoted $1,400/mo for similar features. Your usage data shows you don't use 4 modules you're paying for. Renegotiation ask: 30% discount + drop 2 modules. **3. AWS Reserved Instances — $4,200/mo, $50,400/yr — expires July 15.** Packet: switch to compute savings plan = $3,400/mo, save $9,600/yr. **4. Notion — $260/mo, $3,120/yr — auto-renews June 30.** Low priority — fair pricing, just confirm renewal. **5. Webflow — $48/mo, $576/yr — auto-renews May 22.** Trivial. Auto-approve. **6. Cloudflare Pro — $200/mo, $2,400/yr — expires July 1.** Migration to free tier saves $200/mo if you don't need WAF. **Reply 'execute all' for one-click on each, or pick. Datadog is urgent — 2 days left.**
What you get back
Weekly Monday Lark report: contracts expiring next 90 days, renegotiation packet per contract, calendar reminders for notice deadlines.
Cadence: Weekly Monday 9am scan; emergency report if any high-value contract has <14 days notice deadline.