A checklist for switching contractor software

Rollouts that go badly are often not software problems. More often everything moved at once, during a busy stretch, without a decision about which system held the truth that week.

Before moving anything

• Pick a cutover date and name the day the old system becomes read only
• Decide which records come across, which is usually active clients and open jobs
• Export your client list and contract templates to files you keep yourself
• Write down the three things the new system has to do on day one, and set the rest aside

What to bring

Active clients. Open jobs with current status. Contract and proposal language. Vendor and sub contacts. That is usually enough for a first pass.

What to leave

Closed jobs from earlier years, dead leads, duplicate contacts, and the spreadsheet nobody has opened since spring. Archive the files somewhere safe. Carrying old data across tends to reproduce the original mess behind a new login screen.

An order that tends to work

1. Set up the workspace and assign roles, so people see only their own work
2. Enter your active clients and open jobs. There is no bulk client importer today, so plan this as data entry or send us the list during onboarding
3. Load your contract language and run one real document end to end
4. Train whoever answers the phone first, since intake feeds everything downstream
5. Run both systems for one week on new work only
6. Make the old system read only on the date you picked

Third-party tie-ins like phone, e-signature, and payments are configured on the integrations screen and can be left for later. The system runs without them, so do not hold the cutover for a connector.

Two rules for rollout week

One person owns the switch and answers questions. Any job that starts that week starts in the new system only. Records split across two systems are usually harder to clean up than an imperfect migration.

Thirty days after go live

Check one thing. Is anything still being tracked outside the system? Wherever a spreadsheet survived, that is a workflow the software has not covered yet, and it is worth asking why.