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ThePocketBoss Logo

Business software for handymen and small service teams

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ThePocketBoss - 2026 Pricing, Features, Reviews & Alternatives

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Last updated: September 2026

ThePocketBoss overview

What is ThePocketBoss?

ThePocketBoss connects customer records, estimates, invoices, appointments and jobs for handymen, contractors and small service businesses. Keep repeat-customer details in the CRM, prepare an estimate, schedule a visit and invoice the work. Online payments use eligible Stripe Connect payment links; payment processing fees apply. Inventory and equipment tools record stock quantities and storage locations, and mileage logging records business trips.

Monthly subscriptions are Solo $19.99 for 1 user, Essentials $29.99 for up to 5 users, Pro $49.99 for up to 10 users and Boss $99.99 for up to 25 users. Essentials adds dispatch and crew tools, projects and job costing, QuickBooks Online sync, online booking, receipts, workflows, tasks, Portfolio and reports. Pro adds advanced estimate templates, Smart Routing through selected stops, dashboard analytics, SMS campaigns and banking.

AI Assistant requests included each month are 0 on Solo, 100 on Essentials, 500 on Pro and 750 on Boss. Additional requests use prepaid AI credit at 5 cents each. Boss includes a managed local number and 100 AI Receptionist minutes monthly. Other plans can add the number for $5/month; additional talk time and optional website knowledge use prepaid credit. Messaging and AI usage beyond included allowances, credit reload fees, processing fees and applicable taxes can add cost.

QuickBooks Online sync sends supported customer, invoice and payment records; customer import is a separate action. Smart Routing plans selected stops rather than automatically rescheduling appointments. A 14-day trial requires a credit card. Existing founder customers retain their legacy terms. Check current pricing and feature eligibility before signing up.

Starting price

19.99flat rate /
per month

Alternatives

with better value for money

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ThePocketBoss’s user interface

Ease of use rating:

ThePocketBoss reviews

Overall rating

5.0

/5

2

Positive reviews

100

%

Rating breakdown
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend1.00/10
Rating distribution

5

4

3

2

1

2

0

0

0

0

ThePocketBoss's key features

Most critical features, based on insights from ThePocketBoss users:

Billing & invoicing
Calendar management
Inventory management

All ThePocketBoss features

Features rating:

API
Billing & invoicing
Calendar management
Client management
Contact management
CRM
Customizable fields
Customizable templates
Data import/export
Document management
Employee management
Financial management
For handyman industry
Inventory management
Job management
Mobile access
Project management
Quotes/Estimates
Scheduling
Task management
Workflow management
Work order management

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ThePocketBoss pricing

Value for money rating:

Pricing plans

Pricing details:

Free plan
Free trial
Subscription

Solo

19.99

Per month

Features included:

  • Estimates With E-Signatures
  • Invoices And Online Payments
  • CRM And Customer Portal
  • Inventory, Equipment, And Checklists

Essentials

29.99

Per month

Features included:

  • Estimates With E-Signatures
  • Invoices And Online Payments
  • Scheduling And Dispatch
  • CRM And Customer Portal
  • GPS Time Clock And Timesheets
  • Projects, Job Costing, And Reports
  • Inventory, Equipment, And Checklists

Pro

49.99

Per month

Features included:

  • Estimates With E-Signatures
  • Invoices And Online Payments
  • Scheduling And Dispatch
  • CRM And Customer Portal
  • GPS Time Clock And Timesheets
  • Projects, Job Costing, And Reports
  • Inventory, Equipment, And Checklists
  • Online Booking And Smart Routing

Boss

99.99

Per month

Features included:

  • Estimates With E-Signatures
  • Invoices And Online Payments
  • Scheduling And Dispatch
  • CRM And Customer Portal
  • GPS Time Clock And Timesheets
  • Projects, Job Costing, And Reports
  • Inventory, Equipment, And Checklists
  • Online Booking And Smart Routing

User opinions about ThePocketBoss price and value

Value for money rating:

ThePocketBoss integrations (1)

Integrations rated by users

We looked at 2 user reviews to identify which products are mentioned as ThePocketBoss integrations and how users feel about them.

Stripe logo
Stripe

Integration rating: 5.0 (1)

Integration rating: 5.0 (1)

“It helps sync payroll and employee data with accounting, reducing manual data entry and keeping financial records more accurate.”

SS

Sachin S.

Senior executive HR

Twilio logo
Twilio

Integration rating: 5.0 (1)

ThePocketBoss support options

Typical customers

Freelancers
Small businesses
Mid size businesses
Large enterprises

Platforms supported

Web
Android
iPhone/iPad

Support options

Email/Help Desk
FAQs/Forum
Knowledge Base

Training options

Documentation
Live Online
Videos

ThePocketBoss FAQs

Q. Who are the typical users of ThePocketBoss?

ThePocketBoss has the following typical customers:
Small Business, Freelancers

These products have better value for money


Q. Does ThePocketBoss support mobile devices?

ThePocketBoss supports the following devices:
Android, iPhone, iPad


Q. What level of support does ThePocketBoss offer?

ThePocketBoss offers the following support options:
Email/Help Desk, FAQs/Forum, Knowledge Base

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