Paying Personnel, Drivers & Owner Operators

Tailwind helps you keep track of bills owed to external vendors. It also tracks expenses owed to your employees — whether commissions owed to sales reps for a particular Order, pay for your Driver’s Revenue Splitting or per mile pay for Owner Operators. These outstanding bills can then be paid using the Personnel Pay Wizard for company Employees and the Owner-Operator Pay Wizard for Owner Operators.  Under the AP section, you will find both wizards.

Begin by navigating to the wizard itself, located in the AP section of the left navigation.

Once there, first, select the Pay Date up to which you want to pay your Personnel. Then select the Personnel whose Bills you would like to pay in the ‘Personnel Record’ drop-down. This will bring up all posted, un-paid Bills from on or before the Pay Date and associated with that person. The list also provides some summary information on each bill. The ‘Related Order’ column indicates whether the associated Invoice has been paid by the customer or remains unpaid.


If you wish to add a deduction or bonus to the Personnel payment, you can do with the ‘Add Deduction/Bonus’ button. This will bring up the ‘Add Deduction / Bonus’ screen.

This screen is very similar to the one for adding a Bill, as you are essentially adding a new Bill owed to this Vendor — in the case of a Deduction, it will be a Bill for a negative amount.

Fill out the fields as appropriate for the Deduction or Bonus. This will be easiest if you have already created an Expense Item to cover the different types of deductions or reasons for a bonus that you are likely to use — if you have not, you may want to add those Expense Items before proceeding. If you want to pay the driver or owner operator a bonus (for example, a layover), then the bill will have a positive in the units and the amount you want to pay in the unit rate.  If you are deducting something from the driver, personnel or Owner Op, you will make the Units a negative, and the Unit rate will be the amount you want to deduct. So, a “-1” in the units will deduct, and a “1” in the Unit will pay.

Once you have filled out the Deduction or Bonus information, click ‘Apply’ to return to the Personnel Pay Wizard. The new item should appear in the list.

An excellent article for “Scheduling regular monthly deductions for Owner Operators” is our article titled “Scheduling a Bill,” which will show you how to set up recurring deductions. And to take it one step further, we often want to know YTD amounts for deductions that Owner Operators pay us, like the gathering of escrow or regular monthly insurance deductions. Therefore, the Owner-Operator and the Personnel pay settlement statements will now display a new column showing the YTD amount for the calendar year so an Owner Op or a Company driver can see that at a glance.

Selecting Bills

Select the Bills you want to include in this set of payments by clicking on the ‘Approved’ toggle to the left of each item. You can also use the ‘Select All’ and ‘Clear All’ buttons above the list to approve or un-approve all the listed Bills. Once all the Bills are selected, click the ‘Process Payments’ button on the top right to continue.

Paying Multiple Personnel

If you want to issue payments to multiple Personnel, the process is the same. You can use the Personnel Record drop-down or the ‘Previous’ and ‘Next Personnel Record’ buttons to navigate between Personnel. Bills marked ‘approved’ for each personnel will remain approved even when you navigate to a different Personnel list — so that when you click the ‘Process Payments’ button, they will all be processed at once.

Processing Payments

The ‘Process Payment(s)’ button will bring up the Payment Processing screen.

First, select the account from which you want to pay your Personnel under ‘Account Activity’ — this will bring up all the Approved bills that match the currency of the account you have selected.

If you want to print out the checks and process the payments, you must select Print Checks. Tailwind will also automatically assign a Starting Check # for these payments — if necessary, you should adjust this number to match your checks. You can also add a note to the checks using the ‘Check Note’ field.

Click the ‘Process’ button to complete the Wizard. Any checks to be printed will appear in new tabs in your browser as PDFs for you to print or save for your records. This will also return you to the beginning of the Wizard.

Adding an Advance

You may wish to issue an advance to a particular employee in some cases. To do so, click the ‘Add Advance’ button. This will bring up the Add Advance screen.

Adding an Advance will create a new Bill for the advance amount on the Charge Date and an equally-large Deduction on the Deduct Date. As with Bonuses and Deductions, it may be helpful to create specific Expense Items for your advances.

Once you have filled out the Advance information, click ‘Apply’ to return to the Personnel Pay Wizard. The advance amount should appear in the list and can then be approved and paid, as explained above.

Before you can pay your Personnel, you may have to create a Personnel record for them.

You can use Automatic Payables to automatically add your personnel’s Payables when specific circumstances are met.