Engagement tracking for project managers

Take the friction out of Project Management.

Leeward turns a signed contract into a live engagement — every milestone, date, amount, and the clause behind it, already in place. Then it watches, so you never have to babysit a spreadsheet again.

Free to start · Import your first contract in minutes · No spreadsheet required
PDF
MSA — Northwind Traders.pdf
Signed · 4 milestones · 3 clauses
NW
Website Replatform
Northwind Traders
Billable now
Milestone 3 of 4 · 75% through the engagement
NowBuild & integration · billable on acceptance
NextLaunch & handover · Jul 20
$42,000
The old way

Right now, every engagement is a spreadsheet you built by hand — and then babysit.

Milestone
Date
Amount
Status
Discovery
3/3
12000
done
Design
4/18
18000
?? overdue?
Build
6/6
42000
billable? check MSA
Launch
7/20
16000
Typed by hand
Every milestone & amount, re-keyed
Never alerts you
Overdue & billable — you notice
Single point of failure
Trapped with one person
Clauses vanish
Lost the moment they're a row
No single view
Every engagement its own island — nothing rolled up
02 · Your whole book, one view

Every engagement in one place. Shared with the team.

One live view of what's at risk and what's ready to invoice — visible to your whole team, not trapped with one person. And recurring retainers keep their own cadence, so nothing runs on memory.

app.leeward.co/radar

Radar

Ready to invoice now
$30,000
Contoso — Observability Rollout · Milestone 3 accepted today
4
Active engagements
6 / 14
Milestones · 43% done
4 days
To next sign-off
2
Invoicing points · 30d
Engagements
CO
Observability Rollout
Contoso
Billable now
Milestone 3 of 4 · 75% through the engagement
NowDashboards accepted · today
NextHandover & docs · ~Aug 5
$30,000
NW
Data Platform Buildout
Northwind
Due in 4 days
Milestone 2 of 4 · 35% through the engagement
NowBuild & review · acceptance pending
NextClient sign-off → invoice · in 4 days
$45,000
FB
MINT Security Review
Fabrikam
On track
Milestone 2 of 4 · 40% through the engagement
NowSecurity review · in progress
NextReport draft · ~3 weeks
Client-funded
GL
Cloud Migration
Globex
Invoiced
Milestone 4 of 4 · engagement complete
NowAll milestones complete
NextInvoice sent · 6 days ago
$18,000
03 · Every engagement, one workspace

Open it up — the lead, the milestones, the clause, right there.

Every engagement gets its own workspace: who's leading it — and where the alert goes — the milestone timeline, what's ready to invoice, and the exact clause behind it. Nothing to dig for.

app.leeward.co/contoso/observability-rollout
CO
Observability Rollout
Contoso · performed by Aurora Consulting · Fixed-fee $69,000 · Signed Jun 1, 2026
Billable now
PN
Priya Nair
Lead on this engagement
Leadinvoicing alerts → p.nair@aurora.co
3 / 4
Milestone · 75% through
$30,000
Ready to invoice now
$24,000
Invoiced to date
Aug 5
Next milestone · Handover
Happening now
Dashboards accepted by Contoso
Milestone 3 signed off today by J. Rivera — $30,000 is ready to invoice.
Up next
Handover & documentation
Final milestone, targeted ~Aug 5 — invoices $15,000 on client acceptance.
Milestones & activities4 milestones
Discovery & setupJun 3no invoice
Data pipeline liveJun 24$24,000
Invoiced Jun 26.
3
Dashboards acceptedJul 18$30,000
Accepted today — ready to invoice.
4
Handover & documentation~Aug 5$15,000
Invoicing
Ready now$30,000
Invoiced to date$24,000
Remaining after this$15,000
Source SOW
Contoso_Observability_SOW.pdf
§4.3 — drives Milestone 3
Upon client acceptance of the observability dashboards, Contractor may invoice $30,000, net 30.
From Leeward <alerts@leeward.app>
$42,000 is ready to invoice — Northwind Traders
Invoicing alert
Ready to invoice now
$42,000
Northwind Traders — Website Replatform
Milestone 3 · Build accepted · signed off today
§2.3 · MSA — Northwind Traders.pdf
Upon client acceptance of the build milestone, Contractor may invoice $42,000, net 30.
Review & mark invoiced in Leeward
04 · It watches, you don't babysit

Leeward raises its hand — the moment work is billable, you know.

It surfaces what needs action and tells you the instant a milestone becomes invoiceable under the contract. No more scanning rows to catch what the sheet will never volunteer.

05 · Keep stakeholders updated

One click, a clean report —Updating Stakeholders made easy.

Every engagement exports to a polished PDF — the milestones, the money, the scope — ready to share with clients and execs who need the story, not a login.

LeewardEngagement export|Exported Jul 2, 2026
Engagement

Observability Rollout

Contoso · performed by Aurora Consulting · signed Jun 12, 2026
Billable now
Total contract value
$69,000.00
Ready to invoice now
$30,000.00
Milestone 3 · Dashboards & alerting accepted
Invoiced to date
$29,000.00
2 of 4 milestones
Remaining invoiceable
$10,000.00
1 milestone ahead
Milestones4 milestones · 1 billable now
MilestoneDateInvoiceableStatusAmount
Discovery & instrumentation plan
Apr 18, 2026YesInvoiced$12,000.00
Collectors live in production
May 22, 2026YesInvoiced$17,000.00
Dashboards & alerting accepted
Accepted Jun 30 · signed off by J. Rivera
Jun 30, 2026YesBillable now$30,000.00
Handover & docs
~Aug 5, 2026YesUpcoming$10,000.00
Total contract value$69,000.00
Scope — in
  • OpenTelemetry instrumentation across four production services
  • Collector fleet deployed and tuned in production
  • Dashboards and alert routing for the on-call rotation
  • Runbooks and handover training for the platform team
Scope — out
  • Ongoing 24/7 on-call staffing
  • Custom exporter development
  • Historical backfill beyond 90 days
  • Licence procurement and renewals
Exported from Leeward · never miss the moment work becomes billablePage 1 of 1

Take the friction out of tracking.

Drop in your first contract and watch it become a tracked engagement — on its own.