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.
That's where this role comes in. We're bringing on a Contract Sales Representative to work our existing book of business — the restaurants, venues, dispensaries, arts organizations, retailers, and small businesses that have advertised with City Paper for years and want to keep showing up in front of our readers. This isn't the hunting seat; it's the relationship seat. You'll be the person these advertisers know by name, the one who picks up when they call, and the one who makes sure their next campaign is better than their last.
If you love steady client work, fast follow-ups, and turning a one-issue buy into a year-long partnership, this is your role.
What you'll do
- Work the book. Manage renewals and recurring buys across our existing advertiser base — print, digital, newsletters, and event listings. Keep clients informed on deadlines, specs, and what's coming up that fits them.
- Grow what's already there. Upsell into new surfaces, longer commitments, and bigger packages when it's the right fit. A monthly print buyer who'd benefit from a newsletter sponsorship is your kind of conversation.
- Quote, close, and traffic. Build proposals, send insertion orders, collect creative, and shepherd campaigns from sold to live in coordination with our production and editorial teams.
- Keep the CRM clean. Log every touch, keep the pipeline current, and flag at-risk accounts before they go quiet.
- Be responsive. Most of this job is answering quickly, accurately, and with a Pittsburgh-friendly tone. Clients renew with people who make their lives easier.
- Hand off the big stuff. When a conversation turns into a six-figure brand sponsorship or a complex branded content build, loop in the Senior Ad Sales & Sponsorship Lead. Your lane is the volume business that keeps the paper humming.
Who you are
We're keeping this profile wide. You could come from media sales, an agency account role, small business sales, nonprofit memberships, events, or any seat where you've managed a book of clients and kept them happy.
- You're organized. You return emails the same day, remember which client likes a phone call vs. a text, and never miss a print deadline.
- You can sell without pressure. Our advertisers are neighbors, not leads. You know how to recommend a bigger buy because it's right for them, not because you're chasing a quota.
- You know the City Paper reader — or want to. You can talk credibly about what's happening in Pittsburgh this weekend, because so can our advertisers.
- You're independent. This is a contract role. You set your own hours, work your own pipeline, and report progress weekly. We give you the tools and the warm relationships; you bring the discipline.
- You care about the mission. You believe local independent journalism is worth selling well, and you want to be part of proving that model in Pittsburgh.
Compensation & logistics
- Comp: 1099 contract role. 20% commission on closed revenue, scaling to 30% for high performers who hit defined quarterly thresholds. No cap. We'll walk through the tier structure on the first call.
- Location: Pittsburgh-based. Hybrid and flexible — you'll set your own schedule, but expect to be in-market for client meetings, paper drop days, and City Paper events.
- Hours: Part-time to full-time equivalent, depending on how much of the book you want to carry. We'll size the territory to your bandwidth.
- Reports to: The Publisher.
- Start: Hiring now — we want you in seat ahead of the 2026 selling season.
