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

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.