TreeBossPro Blog — Billing & Payments

Choosing Tree Service Billing Software: Questions to Ask Before You Buy

Every software company says its billing is simple and powerful. The only way to know whether it fits a tree company is to ask the right questions — the ones about how removals, pruning, stump grinding, PHC and storm work actually get billed. This last guide in the series is a checklist for that conversation.

Start With How You Work

In Moving Off Paper Invoices: Switching Your Tree Service Billing to Software we covered switching from paper. Before you switch, make sure the software you pick fits how your company runs.

Write down the kinds of work you bill, how customers pay today and where billing breaks down. If storm season is your biggest problem, focus there. If PHC programs create too many invoices, focus there. The right software solves your actual problems, not a generic list.

Involve your office staff and a foreman in the decision. They are the ones who will use it every day, and they will notice problems you might miss.

Think about where your company will be in three years, too. If you plan to add crews, take on more PHC or pursue commercial accounts, choose software that can grow with you rather than one you will outgrow.

Questions About Invoicing

• Can invoices be created directly from completed jobs?
• Are estimates connected, so approved work carries through?
• Can I use clear line items for removal, pruning, stump grinding and PHC?
• Does it handle sales tax on the lines that need it?
• Can one client have multiple properties for HOAs and property managers?

If invoices are a separate document that has to be re-typed from the job, money will keep slipping through.

Also ask how invoices are sent and what the customer sees. A clear invoice that customers can pay online in a few taps makes a big difference in how fast you get paid.

Also check how easy it is to fix an invoice. Mistakes happen, and software that makes corrections simple saves time and keeps customers happy.

Questions About Getting Paid

• Can customers keep a card on file?
• Can invoices be auto-billed when jobs are completed?
• Can customers pay online, from the invoice or a customer app?
• Does it support deposits and prepayments for big removals?
• Are payment follow-ups automatic?

TreeBossPro does all of these: card on file, auto-billing, online payments, prepayments and payment follow-ups by text and email.

Also ask what happens when a card fails or an invoice goes unpaid. Good software handles those exceptions without manual tracking.

Questions About Recurring and Field Work

• Can PHC programs and pruning cycles be set up as recurring jobs?
• Is there a crew app where crews complete jobs, add photos and notes?
• Does it track chemical applications for plant health care?
• Can customers see visits and invoices in a customer app?
• Are there automated texts and one-tap on-the-way and arrival alerts?

Billing depends on field work. If the crew side is weak, the billing side will be too.

Ask how the customer app works, too. Customers who can see visits, invoices and the live crew map on service day need far less help from your office.

Questions About Price and Commitment

• Is it priced per user, or a flat monthly price?
• Is there a free trial, and does it require a credit card?
• Can I import my customers from a spreadsheet?
• Are there contracts?

TreeBossPro plans are Start at $59/month, Pro at $89/month and Crew at $199/month. They are never billed per user, the 14-day free trial requires no credit card and CSV import brings in your customer list. Compare any option on total cost for your whole team, not just the starting price.

Watch for per-user pricing in particular. Tree crews grow, and software that charges for every climber and groundie gets expensive quickly.

Ask what is included at each plan level, too. Make sure the features you need — invoicing, card on file, online payments, recurring jobs and the crew app — are available at the plan you intend to buy.

Try It With Real Jobs

The best test is to run real work through the software. Import a few customers, send a real estimate, complete a job on the crew app, invoice it and collect a payment. You will learn more in a week than from any demo.

Ask the people who will use it what they think after the trial. If the office and the crews find it easier than what you have now, you have your answer.

That completes this series. If you want to start from the beginning, the first guide covers the whole system, and every guide connects back to TreeBossPro tree service billing and invoicing software. Start a free trial and see whether it fits the way your crews work.