Senior Ad Sales & Sponsorship Lead

Pittsburgh City Paper is relaunching — new ownership, renewed mission, and a rebuilt operation that takes our 30+-year role as the voice of independent Pittsburgh into its next chapter. We’re covering the arts, music, food, politics, and neighborhoods that define this city, and we’re rebuilding the commercial side of the paper to match its ambition to help Pittsburghers better experience everything the city has to offer.

That’s where this role comes in. We’re hiring a Senior Ad Sales & Sponsorship Lead to own revenue across every product the City Paper offers — Our monthly print issue, our website, newsletters, events, and more. This is a builder’s seat. You’ll inherit a trusted brand with deep roots in the Pittsburgh community, a relaunch moment the city is rooting for, and the runway to shape how we package, price, and sell for years to come.

We’re looking for a closer, not a manager. You should want to be on calls, in rooms, and at events, carrying a number yourself. Over time, if you want to build a team under you, we’ll build it together — but the first hire needs to be someone who loves the hunt and can open doors from day one.

What you’ll do

Own the book. Drive new and renewal revenue across every City Paper surface, focusing on top level brand sponsorships for the paper as a whole.Hunt. Build and work a pipeline of Pittsburgh agencies, local and regional advertisers, dispensaries, universities, hospitals, restaurants and bars, arts organizations, real estate, and national brands with a Pittsburgh presence — plus the partners we haven’t thought of yet.Package. Shape how we package and price our inventory across channels — from a simple banner buy to a presenting-sponsor-level event or a multi-platform branded content campaign. Partner with editorial, events, and ops to turn briefs into sellable stories.Sponsor our events. Sell title and presenting sponsorships for City Paper signature events, activations, and the franchises our readers already love. Bring sponsor ideas to the events team as readily as you bring event ideas to sponsors.Build branded content that doesn’t embarrass anyone. Develop branded content and custom campaigns that respect our readers and deliver real results for advertisers. Quality is the bar; we don’t ship work we wouldn’t want to read ourselves.Run the numbers. Own the forecast. Keep a clean CRM, accurate pipeline, and a weekly number you stand behind. Help us learn what’s working, kill what isn’t, and reinvest fast.Represent the brand. You’re a public face of the paper — at events, at industry nights, in Slack DMs with agency planners. You care about Pittsburgh and it shows.

Who you are

We’re deliberately keeping the profile wide. The right person could come from media sales, an agency, events, nonprofit development, venue or festival sponsorships, or a business development or partnerships seat at a brand or startup. What matters is that you close, you’re organized, and you can sell a story.

You’ve closed real money. You have a track record of closing five- and six-figure deals — ideally some mix of advertising, sponsorships, partnerships, or BD revenue — and can walk through specific wins and how you sourced them.You speak multiple buyer languages. You can sit across from an agency planner, a restaurant owner, a university marketing director, and a national brand manager in the same week and adjust your pitch without losing the thread.You know (or will know) this market. You’re in Pittsburgh or moving here, and you want to know everyone in the city who buys or influences a media decision. Existing relationships are a plus; the willingness to build them fast is required.You’re a self-managing operator. You love a clean pipeline, a clear ask, and a fast follow-up. You don’t need a sales ops team to keep you honest — you keep yourself honest.You care about the mission. You believe independent local journalism matters and that selling it well is part of how it survives. You want to be on the team that proves that model in Pittsburgh.

Compensation & logistics

Comp: Competitive base salary plus uncapped commission, structured so strong performance pays like strong performance. We’ll walk through the structure on the first call.Location: Pittsburgh-based, hybrid schedule. Expect meaningful time in-market — at client sites, at City Paper events, and at the industry tables where Pittsburgh buys and sells media.Benefits: Full-time employee with health, dental, vision, PTO, and standard benefits.Reports to: Reports to the publisher.Start: Hiring now — we’d like this person in seat for the 2026 relaunch selling season.