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Top City Advertising Jobs (NOW HIRING)

City Lifestyle

Sales, Advertising

Chicago, IL · Remote

$125K - $250K/yr

... top 10% by home value) * Set your own schedule and grow your business * Represent the City ... Digital product suite -- website, digital advertising, and social media * Recurring revenue model ...

City Lifestyle

Sales, Advertising

Miami, FL · Remote

$125K - $250K/yr

... top 10% by home value) * Set your own schedule and grow your business * Represent the City ... Digital product suite -- website, digital advertising, and social media * Recurring revenue model ...

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As of Aug 22, 2026, the average yearly pay for top city advertising in the United States is $82,994.00, according to ZipRecruiter salary data. Most workers in this role earn between $55,500.00 and $116,500.00 per year, depending on experience, location, and employer.
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Infographic showing various Top City Advertising job openings in the United States as of August 2026, with employment types broken down into 1% As Needed, 73% Full Time, 18% Part Time, and 8% Contract. Highlights an 93% Physical, 2% Hybrid, and 5% Remote job distribution, with an average salary of $82,994 per year, or $39.9 per hour.

Sales, Advertising

City Lifestyle

Chicago, IL • Remote

$125K - $250K/yr

Full-time

Re-posted 4 days ago

Job description

Most people spend their careers building someone else's business. This is your chance to own a business for yourself — but never by yourself.

About the Role

City Lifestyle is opening new territories in Chicago, IL and selecting one driven owner-operator to launch and lead each local edition. As the owner, you'll run your own City Lifestyle market — a hyper-local luxury print magazine and digital media business that reaches the most affluent audience in the community.

You'll operate as an independent owner under a proven model, with the full support of our corporate team behind you.

About City Lifestyle

City Lifestyle is the largest independent publisher in the United States — a hyper-local network of luxury print magazines and digital media operating in 250+ markets across 39 states, with 1,000+ new markets available. We're an 8-time Inc. 5,000 honoree, A+ rated by the BBB, and we deliver more monthly impressions than Vogue and Vanity Fair combined.

Responsibilities

  • Build relationships with local business owners and sell advertising targeted at the most affluent audience in your community (top 10% by home value)
  • Set your own schedule and grow your business
  • Represent the City Lifestyle brand and become the recognized voice of your market
  • Curate the editorial direction of your local print and digital publications
  • Hire and lead a small local team of contractors with our recruiting support — no full-time employees required

What's Provided

  • Exclusive, protected territory — own your market, your clients, and your book of business
  • Comprehensive training — plus ongoing coaching from a peer network of 250+ business owners
  • Plug-and-play launch — start generating revenue in as little as 30 days
  • Full back-office support — design, printing, and distribution all handled for you
  • Custom CRM and prospecting, billing, and proposal tools
  • Digital product suite — website, digital advertising, and social media
  • Recurring revenue model — renewing advertisers compound your book year over year

Who Thrives Here

Publishing and media experience are NOT REQUIRED. We're looking for high performers who've led in industries like:

  • Sales
  • Business development
  • Marketing or advertising
  • Real estate or mortgage
  • Agency, media, or publishing
  • Broadcasters
  • Community leadership or nonprofit

Strong candidates are relationship-driven, competitive, and ready to convert their network into a real, owned, profitable asset. The rest of the team handles all logistics.

Requirements

  • Proven track record in sales, business development, or business leadership
  • Strong local connections in Chicago and the surrounding community
  • Entrepreneurial mindset with the discipline to execute against a proven playbook
  • Full-time commitment to launching and growing the business
  • Willingness to operate as an independent owner under our proven model

Apply Today

Territories are limited. Apply now to start the conversation.

Company Description

City Lifestyle launched its flagship publication, Leawood Lifestyle, in September 2009. Since its launch in 2009 City Lifestyle has grown to be one of the fastest-growing companies in the country according to Inc. 5000 with over 250 locations across the United States. Rated A+ by the BBB.