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

Note: The job is a remote job and is open to candidates in USA. Outside Interactive, Inc. is a leading hub for active lifestyle enthusiasts, providing exceptional content and experiences to millions of outdoor and fitness fans. They are looking for a Senior Sales Account Executive who will focus on prospecting and closing new business in the competitive media market, specifically within the outdoor and active lifestyle sector.

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

Skills

• A demonstrable track record of opening new accounts — not just growing existing ones
• 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
• 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
• Video and OTT/CTV experience preferred
• Programmatic knowledge is a plus

Benefits

• Commission
• Health care
• Vision
• Dental
• Retirement
• Flexible Time Away
• Sick leave

Company Overview