Media Sales Specialist at Pearachute (Chicago, IL)

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Pearachute is building the world’s largest marketplace for kid-friendly experiences.  We exist to help families spend more meaningful time together.  We recently launched nationally, growing our reach by more than 10X with the most important customers in the world...women 25-45. Our expansion allows us to partner with major brands across a variety of sectors (think CPG, clothing, school supplies, big box, and direct to consumer brands). 

Our close-knit team is hiring a Media Sales Specialist to help us grow this new but already profitable line of business. We are looking for an enthusiastic, self-starter who enjoys doing what it takes to hunt for new partners, foster relationships, and develop custom campaigns that will delight both our ad partners and our growing community of families all over the U.S.  We’re looking for someone with drive and creativity to contribute to our larger vision through the unique insights you gain in your role.

In this position, you will be responsible for:

  • Sourcing leads and evaluating prospects that help make parents’ lives easier and empower families to make the most of the time they have together.  
  • Working with the marketing team to craft beautiful and compelling proposals that serve the needs of our clients.
  • Negotiating contracts and campaigns to maximize wins for both the business and our partners. 
  • Measuring and reporting on the performance of campaigns. 
  • Contributing product ideas that enrich our core offering and benefit our clients.
  • Creating new strategies for growth.
  • Observing industry trends to keep Pearachute at the cutting edge of media and content offerings. 

As our eyes and ears, you will be a part of all product planning meetings and will have a true voice on the team.

More about You:

  • You lead with empathy but commit to authenticity.
  • You exude infectious positivity.
  • You understand what it means to be each other’s village--you are willing to help in any way the team needs you, and you are willing to ask for help when you need it.
  • You will strive to create more high-five moments for our customers, activity providers, and business partners.
  • You embrace skinned knees-- you’re not afraid to make mistakes because you know it helps you grow and learn.
  • You’re also smart, fun, and a creative problem-solver.
  • And, you care…a lot.


  • You are great at making connections.
  • You know how to communicate a vision.
  • You excel at pleasant persistence.
  • You dominate a CRM.  
  • You have excellent grammar and writing skills and you aren’t afraid to use the phone.
  • You have good judgement.
  • You can multitask.
  • You see projects through to completion.
  • You are good at asking for and receiving constructive feedback. 
  • You’re motivated to close. 
  • And ideally you have at least three years of experience. 

Compensation will be a competitive base plus commission with the chance to make well into 6 figures.  

More about Pearachute

We are a small team of passionate problem-solvers.  Our offices are in Bucktown next to the Damen Blue Line stop.  Most of us work full-time but some of us are part-time, because we choose to spend more time with our children.  We are venture-backed. We’ve been on Shark Tank. We work really efficiently. We all have a voice. We all care a lot about helping to make parents’ lives easier and about helping businesses thrive.  We’re not all parents, but we all care about inspiring the next generation of conscious, compassionate, and creative citizens.

Our office is cheerful, energizing, and close to great restaurants.

Finally, this role is flexible.  It’s full-time, but you could do part of it from home or on weekends.  And nearly everyone works from home on Fridays. 

We are excited to meet you!


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1564 N. Damen , Chicago, IL 60622

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