Guide 2: Choosing software for a small service business

Start with the work, not the tool

Coming from tech, my first instinct was to set up a full stack of tools on day one. That was backwards. A small crew doesn’t need a platform. It needs the next job booked, done, invoiced, and paid without anything falling through the cracks.

So before you look at any software, write down how one job moves through your business from first call to final payment. That list is your requirements doc.

The five jobs software actually does

Most service businesses need help with the same five things. You don’t need one tool per item, and you might not need all five yet.

1. Capturing leads: where do calls, texts, and form messages land, and who answers them?
2. Estimating and quoting: building a price and sending it in a way the customer can approve.
3. Scheduling: who is where, on which day, with what materials.
4. Invoicing and payments: getting paid without chasing anyone.
5. Bookkeeping: knowing whether you made money this month.

Questions to ask before you buy

• Will the people in the field actually open it on their phones?
• Can I get my data out if I leave? Ask for an export before you commit.
• Does it connect to my bookkeeping, or will I be retyping numbers?
• What happens when it goes down in the middle of a job?
• Is the monthly price per user? What does it cost at twice my current size?

What to skip for now

• Custom builds. Even as an engineer, resist the urge. Off-the-shelf tools are cheaper than your weekends.
• All-in-one suites you’ll use a tenth of. Pay for what you use this quarter.
• Dashboards. If nobody makes a decision from a chart, it’s decoration.

A rule I borrowed from engineering

Treat every new tool like a dependency. Each one adds a login, a bill, a place data can go stale, and something new to train people on. Add one only when the pain of not having it is clear, and review your stack every few months to cut what nobody opens.

• I wrote down how one job flows, start to finish
• I know which of the five jobs hurts most right now
• I tested the export before signing up
• Someone in the field tried it on their phone