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

Outside is a premier hub for active lifestyle enthusiasts, offering best-in-class content and experiences to millions. They are seeking a Senior Sales Account Executive who will be responsible for prospecting, pitching, and closing new accounts in the outdoor and active lifestyle media sector, while also managing and deepening client relationships.

Responsibilities:

• 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

Requirements:

• 8+ years in media sales with consistent, documented achievement against high revenue targets
• A demonstrable track record of opening new accounts — not just growing existing ones
• 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
• 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
• Existing relationships in CPG, Healthcare, Retail/Outdoor, FinSer, Travel/Tourism are a significant advantage