Get Paid 2x Faster with Chicago's #1 Contractor Billing App
Stop chasing payments. Built for Chicago's 28,000+ contractors to get paid faster.
Average time to first payment: 3 days • No contracts
Chicago Contractors Get Paid Faster
Start Getting Paid in 3 Simple Steps
Create Invoice On-Site
Finish the job, create invoice in 30 seconds. Add photos, materials, labor - right from your phone at any Chicago job site.
Send & Track Instantly
Send via text or email. Know when your Chicago clients view it. Automatic reminders ensure you never chase payments again.
Get Paid Fast
Accept credit cards, ACH, checks, Venmo, Zelle - whatever your Chicago clients prefer. Money hits your account in 1-2 days.
Billing Features Chicago Contractors Love
Everything you need to get paid on time, every time
Lightning Fast Invoicing
Create professional invoices in 30 seconds. Templates for HVAC and other Chicago trades save even more time.
Multiple Payment Options
Let Chicago clients pay how they want - credit card, ACH, check, Venmo, Zelle, Cash App. Higher flexibility = faster payments.
Smart Payment Reminders
Automatic, professional reminders get you paid without awkward conversations. Customizable for Chicago business practices.
Real-Time Payment Tracking
See who owes you money, track partial payments, and monitor cash flow across all your Chicago projects instantly.
Client Payment Portal
Give Chicago clients a professional portal to view invoices, make payments, and download receipts 24/7.
Estimate to Invoice
Convert approved estimates to invoices with one tap. Perfect for Chicago's competitive bidding environment.
Real Results from Chicago Contractors
Before PocketBoss
- ✗30-45 days average payment time
- ✗10% of invoices lost or forgotten
- ✗Hours spent chasing payments
- ✗Cash flow problems every month
- ✗Professional image concerns
After PocketBoss
- ✓7-14 days average payment time
- ✓Zero lost invoices - ever
- ✓Automated payment collection
- ✓Predictable, healthy cash flow
- ✓Professional branded invoices
Chicago Contractors Get Paid Faster
"Was owed $45K from various Chicago jobs. PocketBoss helped me collect $38K in the first month with automated reminders. Wish I found this sooner!"
HVAC Contractor
8 years in business • Chicago
"My Chicago clients actually prefer paying online. I get paid in days instead of weeks. The invoice tracking shows me exactly who owes what."
Residential Service Provider
Solo operator • Chicago, IL
Start Getting Paid Faster Today
The billing solution designed for Chicago's 28,000+ contractors
Simple Pricing
per month • unlimited everything
Start 14-Day Free TrialNo credit card • Cancel anytime
The Preferred Billing App for Chicago Contractors
In Chicago's competitive construction market, getting paid quickly is essential for business survival and growth. With 28,000+ active contractors competing for projects worth $8.2B annually, cash flow management can make or break your business.
PocketBoss was built specifically for contractors like you - professionals who need to create invoices from job sites, track payments across multiple projects, and maintain healthy cash flow without hiring a bookkeeper. Our billing app helps HVAC, Roofing, General Contracting, Snow Removal contractors throughout Chicago get paid 50% faster on average.
Whether you're billing for a small repair job or a major renovation project, PocketBoss ensures you never lose another invoice, never forget to follow up on payment, and always maintain a professional image with your Chicago clients.