If you're a citizen of a country for which a US visa is required, you'll need a B1/B2 visa.
To successfully apply for US temporary visitor visa, you'll need to satisfy visa officer of satisfying ties (job, money...etc) in Canada, making you leave the US at the end of your visit. It also applies to trucking, as it's a business (B1) activity.
Family and children are indeed strong ties. Sounds like you're also okay on funds.
But I strongly doubt that Uber would count as a strong tie, as it's easily breakable by simply not coming back to Canada. Don't use that.
Best bet would be to have your new employer provide you with all documents, including salary information and contract, or probably even apply on your behalf.