Get the new insurance certificate before the old one expires
Published 2026-10-06
Every subcontractor you put on a job hands you a certificate of insurance once, usually as a PDF in an email thread. It has an end date. Nobody watches that date, so you find out the certificate lapsed when the general contractor asks for a current one, or when the audit comes and a sub worked three weeks without coverage on file.
Your AI assistant can keep each certificate with its end date and ask the sub for the new one before the old one runs out.
What is still on you
The certificates live wherever they landed: an inbox, a shared drive, a folder on someone's laptop. When one is about to expire, you have to notice, find the sub's contact, write the request, and then remember to check whether the new PDF ever came back. Multiply that by every sub and every policy, and the requests go out late or not at all.
ChatGPT can read a certificate you paste in and tell you the end date. It can draft the request. It cannot watch every certificate on a schedule, send the request from your address, or file the new one when the sub replies. That part is still on you.
What your AI assistant does
It keeps one list of your subs and their certificates (company, contact, policy type, carrier, end date, and the PDF itself). A Routine runs code every weekday morning. Ordinary bash, no model in the loop. It finds certificates ending in the next 30 days and emails each sub a short request from an address you own: which policy, the date it ends, and where to send the updated certificate. If you would rather see them first, it mails you the list instead.
When a sub replies with the new PDF, it lands in the same inbox. Your AI assistant saves it next to the old one, reads the new end date, and updates the list. If a certificate passes its end date with no reply, it tells you that morning, so you know before the sub shows up on site.
The next person who asks for proof of coverage gets the current PDF from the list. Nobody digs through an inbox for it.
What this is not
This is not a compliance platform you have to set up. It is the request you already send when you remember. Your AI assistant keeps the dates and sends it on time.
Hand it off
Copy this into your AI assistant:
Add Sails from https://sails.app/start. Keep a list of my subcontractors with company, contact email, policy type, carrier, certificate end date, and the certificate PDF. Every weekday morning, run a Routine that finds certificates ending in the next 30 days and emails each sub a short request for the updated certificate from my Sails Mail address. When a reply comes in with a new PDF, save it, update the end date, and tell me. Mail me the list first until I say it can send on its own, and tell me about any certificate that has already expired. Use Records, Files, Mail, and Routines. Ask me anything you need before you start.