How to fill a supplemental from HawkSoft with Claude, step by step
- Drag the supplemental into Claude. In the Claude desktop app with FreeBird installed, drag and drop the carrier's blank supplemental PDF into a new chat.
- Name the client. Type something like In HawkSoft I have Prairie Freight, fill out this supplemental for me, and press Enter.
- Let FreeBird pull the HawkSoft data. FreeBird collects the client's data from HawkSoft on its own. HawkSoft can be on the home page or another client's profile, and you can keep working in other apps.
- Let Claude fill and check the form. Claude fills the supplemental, then checks each page with a screenshot and fixes anything that landed wrong.
- Read the review sheet. Claude hands the form back with a review sheet: what it filled from HawkSoft, what it left blank because HawkSoft had no answer, and anything it chose not to use.
- Save the PDF. Click save. The PDF lands in your Downloads folder and stays editable, so you can finish the blanks, print it, or send it to the insured or the carrier.
The supplemental already lives in HawkSoft
Most of what a carrier supplemental asks for is already in HawkSoft: the insured, the address, the vehicles, the radius, the states, what they haul. The questions are just worded differently, so someone ends up copying the data over by hand.
FreeBird is the small app that connects Claude to HawkSoft. It lets Claude look up clients, fill out forms and applications, create certificates and more, so Claude can answer the supplemental from the real client file. FreeBird is made by WhereToBegin.ai and is not a HawkSoft product.
One prompt, then hands off
In the video, Ben drags a trucker supplemental PDF into Claude and types In HawkSoft I have Prairie Freight, fill out this supplemental for me. Prairie Freight is a test client used in the WhereToBegin.ai course. Ben pressed Enter at 8:47 PM.
A message at the top of the screen showed FreeBird collecting data from HawkSoft. HawkSoft did not need to be open on Prairie Freight first. It could have been on the home page or another client, because FreeBird finds the right record itself.
While it runs you can do other work in Claude, step away, or check on it from the Claude app on your phone.
Claude checks its own work
Once Claude had pulled the Prairie Freight data, it filled the supplemental, then went back to verify the pages. It took a screenshot of the form to check itself, caught a small error, and fixed it before handing the form back with a review sheet.
It finished at 8:49 PM. Claude's summary said the supplemental was partially filled from HawkSoft and that many answers were not in HawkSoft, so it left those blank rather than guess. That is the behavior you want on anything going to a carrier.
What got filled, and what was left for you
Filled from HawkSoft: the named insured and their address, the carrier type, vehicles and radius, and the states, plus the truck brokering yes or no and the commodities hauled. On commodities it marked no for chemicals, gasoline, oil, hazardous waste and explosives, because HawkSoft has the client marked as no hazmat.
Left for the insured: the signature and date, who they haul for, and the carrier limits, since the auto policy in HawkSoft is still a prospect with no carrier. Also the questions about cranes and garbage hauling, whether they subcontract and at what percentage, and the payroll. HawkSoft does have $610,000 of driver payroll, but under a different class, so Claude did not use it.
Ben clicked save and the PDF went to the Downloads folder. It is still editable, so you can fill the blanks yourself, print it, or send it to the insured or the carrier. The whole thing took less than four minutes.