From signed SOW to billable alert, in three steps.
Upload a signed contract — PDF, Word, or a photo of the pages. That's the whole setup.
It pulls out the engagement, every milestone, and the exact clause that makes each one billable.
The moment a milestone becomes billable, Leeward emails you — with the amount and the clause that triggered it.
The email you'll never want to miss.
One glance: the amount, the milestone, and the clause in your SOW that makes it billable. Tap once to mark it invoiced.
- Reads your real contract.
- Finds the exact clause that triggers billing.
- Catches the moment it fires.
- Tells you the amount, ready to invoice.
Built by a delivery PM who tracked 8–10 concurrent SOW engagements in spreadsheets — because missing an invoice point is the worst day of the month.
Made for PMs who run contracts in a spreadsheet.
If you juggle several client SOWs at once and track milestones and invoice points by hand, Leeward is the safety net under that spreadsheet — it watches every contract and pings you the moment one becomes billable. No PSA migration, no setup project, no per-seat bill.
Questions a careful PM asks.
You choose what to upload, the AI never files or sends anything on its own, your contracts are never used to train AI, and you can delete any of them anytime. See how Leeward handles your contracts.
There isn't any. Drop in your first SOW and Leeward does the rest — you'll have your first tracked engagement in under a minute.
Leeward shows you exactly what it found, against the clause it found it in, and you confirm every field before anything is saved. You're always the final check.
We'd rather earn a roomful of PMs who'd miss us than charge a handful. Leeward is free while we grow; if we ever add paid tiers, they'll sit below what the heavy tools charge.