Author name: Louisa Weits

1099 vs. W-2 Truck Drivers: What Actually Determines Classification?

Date Published: October 13th, 2026 1099 vs. W-2 Truck Drivers: What Actually Determines Classification? Can a truck driver choose to be paid as a 1099 contractor? What if they have an LLC? What if they own the truck? What if they sign an independent contractor agreement? Trucking companies hear these questions all the time because […]

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How to Switch Truck Drivers From 1099 to W-2 Without Losing Them

How to Switch Truck Drivers From 1099 to W-2 Without Losing Them Date Published: October 12th, 2026 Realizing your truck drivers should probably be W-2 employees is one thing. Actually changing them from 1099 to W-2 is another. You have to decide when the change happens, figure out what their new paychecks will look like,

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Trucking Fleets Grow for Third Consecutive Month as Driver Turnover Falls

Trucking Fleets Grow for Third Consecutive Month as Driver Turnover Falls Published: October 2nd, 2026 Key Takeaways Who Is This For? This report is for trucking-company owners, executives, CFOs, controllers, HR leaders and payroll professionals who want to understand what is happening with driver employment, pay and turnover. The information comes from anonymized payroll data

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When Can You Pay a Truck Driver 1099? What a Real Owner-Operator Looks Like

Published: October 1st, 2026 When Can You Pay a Truck Driver 1099? What a Real Owner-Operator Looks Like There is nothing automatically wrong with paying a truck driver as a 1099 independent contractor. There are plenty of legitimate owner-operators in trucking who operate their own businesses, take on financial risk, make their own business decisions,

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Do You Need a TMS Integration to Outsource Payroll for Your Trucking Company?

Do You Need a TMS Integration to Outsource Payroll for Your Trucking Company? Published: September 30th, 2026 Executive Summary If you are considering outsourcing payroll for your trucking company, one of your first questions may be: Does the payroll company integrate with our TMS? It is an important question, but it may not be the

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Can an Outsourced Payroll Company Really Handle the Complexity of a 200–500 Truck Fleet?

Published: September 28th, 2026 Can an Outsourced Payroll Company Really Handle the Complexity of a 200–500 Truck Fleet? For a trucking company with 200, 300, or 500 trucks, outsourcing payroll is a very different decision than it is for a 20-truck fleet. At this size, payroll is rarely just a matter of entering hours and

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In-House Payroll vs. Outsourced Payroll for a 200–500 Truck Fleet: Which Model Fits Your Company?

Published: September 22nd, 2026 In-House Payroll vs. Outsourced Payroll for a 200–500 Truck Fleet: Which Model Fits Your Company? For a trucking company with 200, 300, or 500 trucks, payroll is not a small administrative task. You may have hundreds of drivers working in multiple states, office employees, mechanics, dispatchers, unusual pay arrangements, garnishments, benefits,

In-House Payroll vs. Outsourced Payroll for a 200–500 Truck Fleet: Which Model Fits Your Company? Read Post »

The 7 Biggest Problems Trucking Companies Run Into When Outsourcing Payroll

Published: September 21st, 2026 The 7 Biggest Problems Trucking Companies Run Into When Outsourcing Payroll Outsourcing payroll isn’t automatically better. In fact, for some trucking companies, outsourcing payroll can make things worse. That’s especially true for larger fleets. A trucking company with 25 trucks may have an owner or office manager who would gladly hand

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How Much Does Outsourced Payroll Cost for a 200–500 Truck Trucking Company?

Published: September 18th, 2026 How Much Does Outsourced Payroll Cost for a 200–500 Truck Trucking Company? For a trucking company with 200 to 500 trucks, the cost of payroll is much bigger than the invoice from your payroll software company. You may have one or more employees working on payroll. You have software costs. Someone

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