You can see how to set up your account correctly to interact with Lightspeed's work orders from QuoteMachine in the following help article.
The video below shows the entire Workflow from Quote to Invoice.
Open any quote that is in the "Won" status
Click the "Create Work Order" button
Note: If you are not logged into Lightspeed Retail when you click the "Create Work Order" button, you will be prompted to authenticate with Lightspeed Retail. Once you have logged in, you can retry the Work Order creation from the quote using the "Create Work Order" button again.