In short
Contractor scheduling software helps small crews assign jobs and milestones, keep track of who is working when, and avoid double-booking people who are off. Work Pilot combines a mobile-first calendar, milestone assignments, working-hours setup and time-off requests in one place.
The problem this solves
- ✕Assignments made in group chats that no one can find later.
- ✕Booking a milestone on a day someone's already off.
- ✕No easy way to see the whole week for the whole crew.
- ✕Missed handoffs between quoting, scheduling and the field.
How it works
Built for the day-to-day of a small contractor crew.
Milestone assignments
Break a job into milestones and assign them to specific people with flexible date ranges.
Team calendar
See every scheduled milestone across the crew, filter by person, week or month.
Working hours & time off
Set each employee's working hours and approve time-off requests. The scheduler warns you before conflicts.
AI reminders
Automatic follow-up nudges so nothing slips before, during, or after the job.
Jobs tied to addresses
Every scheduled milestone is linked to the customer and job address for the field.
Hard-block time-off conflicts
Approved time off blocks new assignments on those dates — no accidental overlap.
Who uses this
Related pages
Frequently asked questions
Can multiple people be assigned to one milestone?+
Yes. Milestones support multi-user assignment and flexible date ranges so a job can have several crew members on the same phase.
Does it block scheduling during approved time off?+
Yes. Once time off is approved, new milestone assignments during those dates are blocked server-side.
Can I see the whole crew's week on one screen?+
Yes. The calendar shows every scheduled milestone with quick filters by person, day, week or month.
Does the scheduler work on mobile?+
Yes. Work Pilot is mobile-first — assign, reschedule and check the week from your phone.