Careers · Advertising Sales Representative

Turn your experience into unlimited earnings

If you have built a track record selling digital or advertising solutions, you already know your value. Winstar Interactive is looking for proven sales professionals who want complete control over their income and want to sell cutting edge advertising technology.

15%Commission on every deal
No capUnlimited upside, lifetime payouts on accounts you manage
1099Independent contractor, fully remote
Sell today’s hottest channels

More to sell means more to earn

Work with premium inventory across every major digital channel, powered by programmatic technology and our independent trading desk.

Connected TV

Streaming audiences at scale.

Digital audio and podcasts

Engaged listeners, premium placements.

Display

High performance display networks.

Digital out of home

Real world reach, digital precision.

Your advantage

Built so you can spend your time selling

Complete control over your income

15% commission on everything you close, with lifetime payouts on every account you bring in. No caps, just upside.

No operational stress

You find, pitch and close. Our team handles strategy, execution, optimization and reporting.

Sell everything

Sell across all four channels for more opportunities per prospect and bigger deals.

Fast deals

Campaigns launch in days, not months. Clients see results fast and come back for more.

Work your way

Remote with full autonomy over your schedule, pace and pipeline.

Recurring commission

Keep earning on client spend for as long as you work with us. No cliffs, no penalties, no surprises.

What you will do

This is about revenue generation

  • Prospect and build your book of business
  • Pitch integrated media solutions to small businesses, brands and agencies
  • Close CTV, audio, display and DOOH campaigns
  • Lean on the Winstar team to execute and deliver
  • Collect recurring commission month after month
This is for you if
  • You have proven you can sell advertising or digital media
  • You have relationships in the local, regional or national ad space
  • You thrive in commission only roles and want unlimited upside
  • You have an owner mentality and want to build a business
  • You are disciplined enough to run your own pipeline
What we need from you

Requirements

01

5+ years in advertising or digital media sales. We want proven closers.

02

Ability to generate new business and close deals independently.

03

Comfort with programmatic, CTV, audio, display or DOOH, or the drive to learn fast.

04

Strong communication and presentation skills.

05

Existing industry relationships are a major plus.

06

Self discipline to run your own business and pipeline.

Ready to own your income?

Apply at careers@wims.com

Send your resume, a cover letter and a short note on why you are ready. Use the subject line “Advertising Sales Representative” and include examples of deals you have closed or accounts you have managed.

Winstar Interactive Media is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.

Winstar Interactive Media
1655 Palm Beach Lakes Blvd., Ste 903, West Palm Beach, FL 33401  |  (877) 452-0953  |  info@wims.com  |  © 2026 Winstar Interactive Media