Overview
The Milestones feature in Worksome allows you to divide a project into smaller, trackable segments, each with its own due date and amount. This structure provides better visibility for managing independent contractors on large-scale or complex projects.
Milestone-based hires are issued as Statement of Work (SoW) contracts, so you will see Statement of Work terminology on the contract and on the Hire page.
Why Use Milestones?
Clear Progress Tracking – Know exactly which parts of a project are done, pending, or awaiting approval.
Phased Payments – Pay contractors in installments based on completed milestones, rather than a single lump sum.
Simplified Project Management – Keep all milestone details (amounts, due dates, PO numbers) in one place.
Who Can Use This Feature?
Independent contractor hires only. Milestones are not available on payroll hires, and selecting Milestones means Worker Classification and payroll options do not apply to the contract.
Your company needs it enabled. Contact Worksome Customer Support to switch milestones on for your company — it is not a setting you can change yourself.
The contractor needs a business entity set up. If the contractor you are hiring has not set up a business entity, or can only work through payroll, the Milestones option will not appear. Ask them to complete their business setup first.
1. Create a Hire with Milestones
Step 1: Start a Direct Hire
Go to the Job Triage Page
Select Direct Hire.
Note: The Milestones option only appears when you create a Direct Hire using a new brief. It is not available if you hire from an existing job post, or through Find Talent — in those cases, consider listing the milestones in the job description instead. Either way, you can still add milestones later, once the hire exists.
Step 2: Choose the Milestones rate
Pick “Milestones” in the Rate field
In the Rate field, choose Milestones.
If you do not see the Milestones option, check all three of these: you are creating a new brief rather than hiring from an existing job post, milestones are enabled for your company, and the contractor is eligible — see Who Can Use This Feature? above.
Complete Required Fields
Milestone name
Due date
Amount
PO number (only if the Hiring setting “Require PO number on contracts” is enabled. If multiple Milestones are added, each Milestone must have a PO number.)
Total Contract Amount
All milestone amounts are summed and shown as a Total at the bottom of the milestone list.
Classification Disabled: When Milestones are selected, Worksome Classify is bypassed and payroll options are disabled for this contract.
2. Offer & Review Milestones
Step 3: Offer the Hire
Once the hire is created and offered, both you and the contractor can see the milestones on the Hire page, in the Milestones section of the overview.
Step 4: Confirm the Statement of Work
Milestone hires include a Statement of Work confirmation step. Open the hire and use Review Statement of Work to confirm it.
Once confirmed, the hire shows a SoW status confirmed badge.
Step 5: Download the Booking Contract
Standard & Custom PDFs will list each milestone in a dedicated section.
The Rate Box at the top shows the total of all milestones.
3. Managing Milestones
Step 6: Edit Milestones
Open the milestones view
On the Hire page, either open the Manage menu and choose Manage milestones, or click Manage on the Milestones card in the overview.
This opens the Milestones details view.
Click “Edit”
Adjust the milestone name, due date, amount, or PO number as needed.
Contract Revisions
Any change except to the PO number alone will trigger a new contract version the contractor must sign again. You are warned before saving.
Locked Milestones
If a milestone has a pending or approved payment request, it will be greyed out and cannot be edited.
Step 7: Add or remove milestones later
You are not limited to the milestones you set at hire time. From the same Milestones details view you can add new milestones, or delete ones that are not yet in use. The contract total updates automatically, and as with editing, the contractor will need to sign the new contract version.
Milestone Status Icons
Green: Completed (payment request approved).
Orange: Pending approval (payment request submitted).
No icon: In progress (no payment request yet).
The status column only appears once at least one milestone has a payment request against it, so on a brand-new hire you will not see it at all.
Step 8: Approve Payment Requests
When a contractor sends a payment request for a milestone, you can approve it.
Approved milestones update to a green completed status.
💡 Tip: The Milestones details view shows exactly which milestones are done, pending, or have no payment requests yet, helping you track your project timeline.
Need Help?
Chat: Click the chat icon in your Worksome dashboard.
Email: hello@worksome.com
By leveraging milestones, you ensure your team and contractors have clarity on deliverables, deadlines, and payments—all in one place.