Estimate Automation

• ClickUp fires on every task update, so the workflow had to tell an edit that matters, to status, assignee or estimate fields, from one that does not
• Requirements can sit in attached PDFs as well as the description, so both had to be read together
• An AI-drafted estimate cannot go anywhere on its own authority, so a named team lead had to sit between the draft and anyone else

A salesperson creates or edits a task in ClickUp, and the trigger fires. A code step compares the status, assignee and estimate fields to decide whether anything meaningful changed; if not, the run stops there. A task with no description and no attachments gets a comment straight back, mentioning its creator and asking for one or the other. Otherwise the attached PDFs are downloaded, their text is extracted and combined with the description, and GPT-4o classifies the whole request: whether it is clear what the task is, whether it is an estimate or a test task, whether the information is enough and if not what is missing, which category the work falls under, whether one of the company's departments covers it, and whether the task sits in the right list. Any failure becomes a specific comment to the creator, and their next update triggers the same checks again. When everything passes, a second model drafts the estimate in phases and tasks with hours, the workflow writes it to a Google Doc, and a comment with the link asks the matching department's team lead to approve it, naming the main category first when the work spans several.

The workflow never sends an estimate to anyone. It drafts one into a Google Doc and asks a named team lead, from the department the work falls under, to approve it, so a person stands behind every estimate. The same thinking runs through the failure paths: a request that cannot be estimated is never dropped silently. It gets a comment that says exactly what is wrong, whether that is missing information, a test task, a category no department covers, or the wrong list, so the salesperson knows what to fix, and the fix itself runs the checks again.

All of it. I designed and built the whole workflow alone: the trigger and change detection, the attachment extraction, the classification prompts, every comment path, and the estimate generation into Google Docs.