Jobs at Winning Assistants

What Winning Assistants' application asks

Across the 2 application forms Otto has filled at Winning Assistants: 25 distinct questions, 22 of them usually required. A single application works out at about 14 minutes once you have your details to hand. It runs on Workable.

16 are Winning Assistants’s own, not boxes every form has:

• is there any additional information you’d like to share that may help us better understand your…
• please attach a link to your creative portfolio and/or case studies.
• do you have experience specifically running ads to book sales calls/consultations for companies? if yes…
• what is your date of birth?
• using loom.com, please record yourself answering the following questions and send us the video link once…
• what was the largest monthly meta ads budget you personally managed for one business, and what results did…
• what monthly rate are you seeking in usd?
• are you able to join video calls (zoom, google meet, etc.) during your shift and turn on your camera if…

and 8 more.

Read off the forms themselves, last checked 2026-09-13, because Otto fills them in and has to read them first. Roles differ, so the estimate is per application rather than for the list above: each question counts for its cost times how often this employer actually requires it. A written answer is 2½ minutes, a dropdown 12 seconds, a yes/no 5 seconds, attaching a file 45 seconds. The list leaves out name-and-email boxes and anything Workable puts on every employer’s form.