Seeking advice on which legal forms to use for hiring contract work outside of freelance platforms (e.g. Upwork).
What sorts of documentation do you need to be signed in both directions, and what sorts of tax forms should I be aware of?
Legal-wise it's up to you. You set the terms of the contract. You typically want to have terms defining the scope of work, making it clear that all work product is the property of your company, payment conditions, etc.
Tax-wise, if you want to be buttoned-up you should ask the contractor to complete a W-9 and then keep it for your records in case the IRS comes calling. Then, you should file a 1099-MISC by January 31 the year after the contractor performed work and send a copy to the contractor and a copy to the IRS.
Details, forms, and instructions here.
www.lawvolcano.com - we focus on providing legal forms for this purpose
Company NDA: Company provides, contractor signs
Contractor Agreement: Contractor provides, both parties sign
Tax Form 1099: contractor fills out.
This has been standard for the last ~6 freelance gigs I have done, including 2 this year.