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

About the role

This role is centered on new business development within the outdoor and active lifestyle media space. The Senior Sales Account Executive will be responsible for the entire sales cycle, from prospecting and pitching to closing deals and nurturing client relationships. Success in this position means consistently meeting and exceeding revenue targets by securing new accounts and expanding existing partnerships.

The executive will work with a variety of digital media products, including video, OTT/CTV, branded content, and sponsorships. They will collaborate with internal editorial, marketing, and strategy teams to ensure successful campaign delivery and to communicate client needs back to the organization. This collaborative environment supports the sales effort by providing resources for effective client solutions.

A key aspect of this role involves building and maintaining a strong presence in the industry. This includes attending events to network with brands and agencies, establishing credibility, and positioning Outside Digital as a preferred partner for advertising budgets. The ability to present confidently and influence decision-makers at all levels, from brand managers to CMOs, is crucial for achieving these objectives.

The base salary for this role ranges from $63,250 to $109,250, with additional commission opportunities.

Skills that matter here

• Salesforce: This tool is used to manage the sales pipeline, track progress, and ensure accurate revenue forecasting.
• Google Suite: Proficiency in Google Suite is required for daily operational tasks and communications.
• digital media sales: A strong command of digital media sales strategies is essential for pitching and closing deals across various platforms.
• video: Experience with video advertising is preferred, as it is a key offering to clients.
• OTT/CTV: Knowledge of Over-the-Top and Connected TV advertising is preferred for addressing client needs in these growing areas.
• programmatic: Understanding programmatic advertising is a plus, contributing to a broader ability to solve client problems.

Who this role suits

• A person who thrives on opening new accounts and has a demonstrable history of generating new business, not just managing existing ones.
• Someone with at least eight years of experience in media sales, consistently achieving high revenue targets.
• An individual who possesses deep knowledge of the Chicago media and advertising landscape and has an established network of agencies and brands.
• A confident presenter and persuader capable of influencing various stakeholders, from brand managers to CMOs.

From the employer

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.

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.
• We are committed to fostering a diverse and inclusive workplace. Outside Inc is an Equal Opportunity Employer.