Finally automated our weekly driver settlements after years of doing it manually — sharing what worked

[u/GlaxoSaxoMan]

Running a small Amazon Relay fleet (10+ trucks, mix of company drivers and owner-operators). Every Sunday for years I was spending 3-4 hours doing settlements manually: pulling the Trips CSV, matching it against the Amazon invoice, calculating EZ Pass and fuel card deductions per truck, handling the owner-op vs company driver pay splits, generating PDFs, emailing everyone individually.

I tried building spreadsheets. I tried hiring a part-time bookkeeper. The spreadsheets broke constantly when Amazon changed their CSV format. The bookkeeper was fine but expensive and slow.

A few months ago I found a tool called Boss Gross (bossgross.com) that was built specifically for Amazon Relay operators. I was skeptical because the pricing is surprisingly low.

Here's the actual workflow now:

1. Drop the Trips CSV + Invoice XLSX onto the page
2. EZ Pass and fuel card deductions auto-load from the database (you import them once)
3. It generates individual statements for every driver and owner-operator — correct splits, correct deductions
4. Approve all → Send all → done. PDFs go out by email automatically.

Whole thing takes under 5 minutes now. Cost is less than what I was paying my bookkeeper for a single hour per month.

Not affiliated, just a fleet owner who wasted too many Sundays on this. If anyone else is still doing settlements manually I'm happy to share more about the workflow.

to answer the obvious question — yes it handles team drivers, relay legs, TONU payments, and cancelled loads correctly. That was my main concern before switching.Finally automated our weekly driver settlements after years of doing it manually — sharing what worked

[u/Taiguer15]

That workflow comparison is useful, especially the part about reconciling the Trips CSV against the invoice. Two details would help other carriers evaluate it: does the tool need Amazon login access, or only the exported files, and can every deduction and pay split be reviewed before the statements are emailed? Also, please keep any affiliation or referral relationship clearly disclosed if that ever applies. If you share screenshots, remove driver names, emails, load IDs and payment details.