Handyman Business Software Built for Owner-Operators
Last updated: September 10, 2026
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. Looking for a detailed comparison? See our guide to the best handyman software options available today.
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.
From $19.99/month (Solo, one user) to $99.99/month (Boss, up to 25 users). Self-serve setup.
14-day free trial • No contracts • Cancel anytime
See Pocket Boss in Action
Real screenshots from the app. One dashboard for your money, jobs, and clients, with nothing buried in menus.
Handyman Business Management Without the Office Overhead
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.
From $19.99
Four plans, from one user to 25.
Estimates, Scheduling, Invoicing, and CRM in One Handyman App
Pocket Boss is built for owner-operators, not dispatch-heavy office workflows. It combines estimating, invoicing, scheduling, and customer management in one simple platform.
Service call management
Track repair and maintenance Jobs on every plan. Essentials and above add Projects for larger scopes and job costing.
Scheduling and dispatch
Keep your repair visits on the calendar on every plan. Essentials and above add crew assignments and dispatch for working with helpers.
Estimates and job pricing
Build a scope and price for the work on-site. Keep the estimate with the customer record and convert it to an invoice when the job is done.
Time tracking
Track hours per job for accurate billing and better time management.
Customer records and job history
Keep contact details, job notes, estimates, and invoices together so you can look up the work when a customer calls again.
Invoices and payment tracking
Send the invoice, check its payment status, and record cash or check payments. Online card and eligible ACH payments are available with the processing terms below.
Quick job entry
- Client name + address
- Job notes
- Scheduled time
- Materials
Job Management for Every Type of Handyman Work
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. Need a broader solution that works across trades? Check out our contractor business software overview.
- Track every job, no matter how small
- Bill accurately for time and materials
- Look professional with clean estimates and invoices
From a Handyman Service Call to a Paid Invoice
Book the service call
Add the customer, address, job notes, and appointment. Keep the visit on your calendar instead of relying on a text thread.
Estimate and complete the work
Write down the scope and price before starting. Track the time and materials used as you complete the repair.
Send the invoice
Convert the estimate into an invoice and check it against the completed work. Send it to the customer from your phone.
Track payment and history
Check whether the invoice is paid or outstanding, record offline payments, and keep the job details for the next visit.
Compare Handyman Business Software
High-level comparison focused on pricing approach and fit.
| Category | Pocket Boss | Other tools |
|---|---|---|
| Pricing approach | $19.99/month (Solo, one user) to $99.99/month (Boss, up to 25 users) | Pricing, seats, and add-ons vary by vendor |
| Best fit | Solo handymen and small crews | Office-supported or larger teams |
| Online payments | Cards and eligible ACH through Stripe; fees come from your payout, not your customer | Varies by platform and plan |
For detailed competitor comparisons, see Best Handyman Software, Jobber Alternative, and Housecall Pro Alternative. For online payment fees and payout timing, see payment processing details.
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. Send a secure payment link by email or text and accept card payments through Stripe, plus ACH Direct Debit when Stripe activates it for your account. Pocket Boss deducts 0.5% from card payments and 0.25% (capped at $25) from ACH payments from your payout; nothing is added to what your customer pays. You can also record cash, check, and other offline payments.
Is Pocket Boss handyman management software or just invoicing?
Scheduling, standard estimates, invoicing, payments, customer records, and Jobs are available on every plan. Essentials adds crew dispatch, projects, and reporting; Pro adds tools such as Smart Routing and tiered estimates.
Does it handle handyman scheduling and dispatch for a small crew?
Yes. Essentials and above include crew dispatch: book jobs on a shared calendar, assign a helper, and let each team member see their day on their phone. Solo includes your own appointments and Jobs.
Is there a handyman scheduling app for my phone?
Yes. Pocket Boss runs as an iPhone and Android app and on the web. Every plan includes appointments. Essentials adds the online booking page, crew dispatch, and text messaging. Smart Routing on Pro and Boss plans a driving route through the stops you pick for the day.
Is Pocket Boss a handyman CRM?
Yes, the CRM is included. Every customer has a record with contact and property details, job history, and a timeline of each estimate, invoice, payment, appointment and message, most of it logged automatically. You also get follow-up reminders, a requests inbox for new booking and lead requests, a private star rating, and a Leave a Review button that texts your review link to the customer on Essentials and above, where text messaging is included.
Can I use it as handyman invoice software?
Yes. Turn an approved estimate into an itemized invoice, send it by email or text with a payment link, and see when the customer viewed it. Optional automatic reminders follow up on unpaid invoices at 3, 7 and 14 days past due, and invoices sync one way to QuickBooks Online on Essentials and above. Sending by text also requires Essentials or above; email invoicing is available on every plan.
Can I use it as handyman estimating software?
Yes. Build estimates on-site from your phone, reuse standard templates for common jobs, and convert an approved estimate to an invoice in one tap. Tiered and sectioned estimate templates require Pro or Boss.
Is there a free trial?
Yes. Start a 14-day free trial. Cancel anytime.
What's included in each plan?
PocketBoss plans currently run from $19.99/month (Solo, one user) to $99.99/month (Boss, up to 25 users), all with the documented core workflows, including invoicing, scheduling, estimates, CRM, Jobs, and payment recording. Optional usage-based services and online processing are priced separately. Review the current Terms before purchasing.
Match the tools to your plan
Tools for Estimates, Follow-Ups, and Field Work
E-Signatures on Estimates
Customers can add a drawn signature when approving an estimate in the portal. Standard estimates and the customer portal are available on Solo and above.
QuickBooks Online Sync
On Essentials and above, connect QuickBooks Online to sync invoices and their payments. Enable automatic sync or run a manual sync, then review the sync status.
Optional Review Requests
Choose review requests after paid invoices or completed appointments. Delivery follows your enabled triggers, channels, contact details, and cooldown settings.
Invoice & Estimate Follow-Ups
Enable email reminders for eligible overdue invoices and unanswered estimates. The reminders use the document status and your follow-up settings.
Job Checklists & Reports
Attach a checklist to an appointment, record completed items, and send its report by email. Available on Solo and above; sending the report is a separate action.
Crew Time & Dispatch
Manage employees, dispatch, and crew time on Essentials and above. Solo includes the separate job timer for one-person work.
Text messaging requires Essentials or above and follows plan allowances and usage charges. Compare current plan inclusions.
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Pricing and features may change. Online payment processing uses Stripe; Stripe fees and approval requirements apply. All trademarks are property of their respective owners. This page was materially reviewed on August 17, 2026.