The core test is whether the software removes re-entry. If a booked load has to be typed again into dispatch, and the delivered load typed again into invoicing, the tool is adding steps rather than removing them.
Document handling is the next thing to check. Rate confirmation, BOL, POD, weight ticket, and lumper receipt should live on the load, capturable from a phone, and pull automatically into the invoice. Chasing paper is where small carriers lose the most time and money.
Accessorials should be first-class, not an afterthought. Detention, layover, stop-offs, and tarps need to be as easy to add and bill as the linehaul rate, because that is where thin loads become profitable ones.
Integrations matter in proportion to what you already run — ELD for hours and location, accounting for the books, load boards for spot freight. A tool that forces a second system of record for any of those is creating work.
Finally, confirm you can get your data out. Loads, documents, and financial history in a standard export format is what keeps a switch from becoming a trap later.
Terms in this answer: Accessorial Charge, Rate Confirmation, Proof of Delivery (POD)
In Trailflow: dispatch.