Senior Sales Account Executive – Chicago/Midwest (Outdoor & Active Lifestyle Media)

We're looking for a proven new business driver, living and networking in Chicago, to join our sales team. This is not a relationship-maintenance role. We need someone who wakes up thinking about pipeline, thrives on prospecting, and gets genuine satisfaction from opening doors that weren't open before. If you can close new business in a competitive media market and you're passionate about the outdoor and active lifestyle space, we want to hear from you.

What You'll Do

• Prospect, pitch, and close net-new accounts — this is the core of the role. You own your pipeline from first contact to signed IO.
• Once you've won the business, deepen those relationships — growing spend, expanding partnerships, and becoming a trusted advisor to your clients.
• Confidently pitch digital, video, branded content, OTT/CTV, sponsorship, and events — whatever it takes to solve a client's problem.
• Use Salesforce to manage the pipeline, forecast accurately, and stay ahead of revenue targets.
• Show up at industry events, build credibility with brands and agencies, and make Outside the first call when budgets open.
• Partner with editorial, marketing, and strategy teams to deliver strong campaigns and bring client needs back to the table.

What We're Looking For

• A demonstrable track record of opening new accounts — not just growing existing ones. We will ask for specifics. New business generation is a non-negotiable requirement of this role.
• 8+ years in media sales with consistent, documented achievement against high revenue targets.
• Must currently live in the Chicago market with deep knowledge of the local media and advertising landscape and an established agency and brand network.
• Strong command of digital media sales; video and OTT/CTV experience preferred. Programmatic knowledge is a plus.
• Existing relationships in CPG,  Healthcare, Retail/Outdoor,  FinSer, Travel/Tourism are a significant advantage.
• Proficient in Salesforce, Google Suite, and curious about AI-driven tools like Gong, ChatGPT, and Gemini.
• You can present, persuade, and influence at every level — from a brand manager to a CMO.
• You don't have to be a professional athlete, but you should understand and care about the audience we serve.

Why Outside

This is a rare opportunity to sell at the intersection of premium media and a category people are genuinely passionate about. You'll represent brands and platforms that riders, runners, and adventurers actually seek out — and you'll do it at a company that's growing. If you're competitive, driven, and ready to build something, let's talk.

What We Offer:

The expected base salary for this role is between $100,000 and $130,000. Additional compensation includes commission. Benefits include health care, vision, dental, retirement, Flexible Time Away, sick leave, and more. This salary range is merely an estimate and may vary based on an applicant’s location, market data/ranges, an applicant’s skills and prior relevant experience, certain degrees and certifications, and other relevant factors.