Handyman Software Built for Owner-Operators
Last updated: Dec 2025
Pocket Boss is handyman business software built for owner-operators and small crews who do the work and run the business. Create estimates on-site, schedule jobs, send invoices, and get paid fast without admin overhead.
In short: Pocket Boss is handyman software for owner-operators who want to schedule jobs, invoice quickly, and get paid without complex setup.
Who Pocket Boss is best for:
- Solo handymen and small crews doing residential service work
- Pros running multiple small jobs per day
- Anyone who wants job → invoice → paid without office overhead
Built for owner-operators and small crews (1-5 users).
$19.99/month (up to 3 users). Set up in about 5 minutes.
14-day free trial • No contracts • Cancel anytime
Simple, Mobile-First, and Fast
Simple
Easy to use. Built for the way handymen actually work.
Mobile
Works anywhere. Run jobs and invoice from your phone.
Fast
Quick setup. Go from job to paid with fewer steps.
$19.99
Flat monthly price for up to 3 users.
Everything a Handyman Needs
Pocket Boss is built for owner-operators, not dispatch-heavy office workflows.
Service call management
Track repair requests, maintenance jobs, and home improvement projects in one place.
Flexible scheduling
Book appointments, manage your calendar, and avoid double-booking.
Quick estimates
Create estimates on-site and convert them to invoices when the job is done.
Time tracking
Track hours per job for accurate billing and better time management.
Client management
Keep client details, job history, and notes organized.
Easy invoicing
Send invoices fast and record payments your way.
Quick job entry
- Client name + address
- Job notes
- Scheduled time
- Materials
Perfect for Every Type of Handyman Job
From quick fixes to day-long projects, manage your work without losing track of the small stuff.
Small Jobs Add Up
Handymen handle dozens of small jobs that are easy to forget, underbill, or lose in the shuffle. Pocket Boss keeps everything organized so nothing falls through the cracks.
- Track every job, no matter how small
- Bill accurately for time and materials
- Look professional with clean estimates and invoices
Get Started in Minutes
Book jobs
Schedule appointments easily.
Complete work
Track time and materials.
Send invoice
Bill clients instantly.
Get paid
Accept any payment method.
Compare Handyman Business Software
High-level comparison focused on pricing approach and fit.
| Category | Pocket Boss | Other tools |
|---|---|---|
| Pricing approach | Flat $19.99/month (up to 3 users) | Often tiered pricing and per-user fees |
| Best fit | Solo handymen and small crews | Office-supported or larger teams |
| Setup | Quick start | More configuration as needs increase |
For detailed competitor comparisons, see Jobber Alternative and Housecall Pro Alternative.
Frequently Asked Questions
What is handyman business software?
It's an all-in-one tool to manage scheduling, customers, estimates, invoices, and payments so you can run jobs and stay organized.
Does it work for a one-person handyman business?
Yes. Pocket Boss is built for owner-operators and small crews that want simple workflows without office software.
Can I create estimates on-site with my phone?
Yes. You can build an estimate on your phone, then convert it to an invoice when the job is done.
Can clients pay invoices online?
Yes. You can email invoices and record payments. Online payment options depend on your payment setup.
Is there a free trial?
Yes. Start a 14-day free trial. Cancel anytime.
What's included in $19.99/month?
Up to 3 users, invoicing, scheduling, estimates, payments, and client management. No contracts. Cancel anytime.
Join Handymen Growing Their Business
Stop losing track of jobs and payments. Run your handyman business like a pro.
Credit card required • Cancel anytime
Pricing and features may change. All trademarks are property of their respective owners.