The form was never the problem

The brief

Make a scary hiring form easier to finish

Upwork was expanding into global payroll with AnyHire, a product that let businesses hire and pay freelancers abroad. The onboarding form was long and people dropped out of it. I was brought in to smooth that out.

What I found

The form was doing its job

Shortening the form helped a little, and then it stopped helping. The real snag sat at the end, in a required classification step where clients had to declare whether a worker counted as an employee or a contractor. For experts who already knew the answer, being forced through it felt like being quizzed on their own job.

The reframe

That step wasn't advice, it was liability

Classification looked like helpful guidance. It was really deciding who was on the hook if a worker was ever misclassified, a legal and financial call dressed up as a form field. Treating it as advice made confident users feel second-guessed, and made unsure users commit to something they didn't understand.

The work

What I shipped

• Made classification optional, so experts move fast and only the unsure get walked through it.
• Added a one-time intro that sets expectations and shows cost early, before the first hard decision.
• Rebuilt the long form into a clear step-by-step flow from the existing design system.

Impact

It uncovered demand we weren't looking for

At a 10% rollout the flow added 250 clients and lifted form completion by 40%. It also surfaced strong demand for converting freelancers into full-time hires, which became the team's next bet.