01 What kind of product is being sold?
Separate the software function from the labor arrangement. A marketplace may introduce independent businesses; a scheduling tool may serve an employer; a payroll processor may move money without becoming the employing entity; and a managed staffing service may coordinate agencies. Marketing pages often blend these layers. Ask the seller to diagram the contracting, payment, insurance, and worker-support relationships for the exact service tier under consideration.
Authority to review: New Jersey Independent Contractor Test
02 Which entity appears in the worker record?
A generic statement that shifts are W-2 does not name the employer. Request the legal name that is expected to appear on wage statements and tax forms, plus its role in withholding, unemployment insurance, workers' compensation, and record retention. If a professional employer organization, payroll company, franchisee, or downstream supplier is involved, show where it enters the chain. Reconfirm the mapping whenever the geography or service package changes.
Authority to review: DOL Enforcement Update
03 What decisions are encoded in the app?
Product settings can reveal how the arrangement operates. Review who sets compensation, publishes mandatory instructions, controls acceptance windows, tracks attendance, approves hours, imposes ratings, restricts future access, or resolves substitutions. Those facts do not produce an automatic classification answer, and different laws weigh evidence differently. They do give reviewers something more reliable than a screenshot bearing a compliance badge.
Authority to review: IRS Publication 15-A
04 Where can the model vary?
Some vendors use different structures by state, client, role, order size, or worker cohort. Put the selected model, employing or engaging entity, and approved subcontractors into the contract record. Require notice before a substitution. A due-diligence memo should also list unresolved exceptions and the person authorized to accept them; silence should not be interpreted as a uniform national arrangement.
Authority to review: New Jersey Independent Contractor Test