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Event Promoter / Flyer Distribution — Vintage Fashion Pop-Up (1099 Independent Contractor, Fixed Fee + Commission)

We are hiring independent contractors to drive traffic and sales for a vintage fashion pop-up event running July 16-19 on Chicago's Northwest Side.

Event Promoter's name goes on the flyers, customers mention it at checkout, and the candidate would earn a commission on every sale tracked. 

The flat fee covers the distribution work. The commission is where motivated people make this worth their time. You'll select one of two zones (Six Corners/Portage Park or Harlem-Irving/Jefferson Park) and you choose your own days and times between Thursday, July 16 and Saturday, July 18.

We run multiple ventures across retail, events, and consulting. Strong performers will be considered for future paid sales roles, though no future engagement is guaranteed. We're looking for people who see this as a foot in the door, not just a one-off gig.

Compensation:

  • $75 flat fee per zone, paid upon completion
  • Commission on event sales tracked to your name (rate and tracking method specified in the contractor agreement)

Note: the hourly figure shown on this posting is an estimated equivalent. Actual compensation is the flat fee plus commission, per written agreement.


Deliverable:

  • Distribute 300-400 flyers hand-to-hand at high-traffic times you choose
  • Hand-to-hand only. No posting on poles, windshields, storefronts, or public property. No stacks or bulk drops.

    Contractors are responsible for complying with all local distribution ordinances.
     
  • Photo check-ins confirming distribution
  • Complete by 2pm on Saturday, July 18
     

Details

  • Engagement type: 1099 Independent Contractor
  • Engagement is subject to a signed independent contractor agreement
  • You set your own schedule within the window
  • Flyer pickup arranged near the venue
  • Two zones available

 

To apply, please answer these questions in detail. 
Complete answers to all questions are required for consideration:

  1. Have you ever sold anything, in any context? Retail, Poshmark, DePop, fundraising, door-to-door sales, a side hustle. Please tell us about it.
     
  2. This role pays commission on sales tracked to the candidate's name. What would you do differently than just handing out paper?
     
  3. You're heading out on a Saturday to work your zone. Walk me through your plan to maximize sales?
     
  4. Someone takes your flyer and says they don't really do vintage. What do you say back?
     
  5. Why is this role a good fit for you, and how would you approach it to get the most out of it?
     
  6. What's your favorite vintage era, designer, or find?
     
  7. Which zone works better for you: Six Corners/Portage Park or Harlem-Irving/Jefferson Park?