Vice President, Sales

City Cast is a national network of local podcasts, newsletters, and social channels dedicated to helping people fall in love with the cities they call home. Through deeply local storytelling and trusted voices, we connect engaged audiences with the brands, organizations, and ideas that matter to them, at scale and at the neighborhood level. 

We're hiring a Vice President of Sales to own advertising and sponsorship revenue growth across the City Cast network. Reporting to the Chief Commercial Officer, this leader will partner with the CCO on strategy and own its execution end-to-end–leading our team, running a disciplined sales process, and delivering against ambitious revenue goals. This is an operator's role for someone who has scaled multi-market or network sales organizations, knows audio and digital advertising, and is energized by the challenge of turning a differentiated local-first network into a category leader.

Deadline to apply: June 18, 2026

• Own the number. Deliver and exceed annual advertising and sponsorship revenue across City Cast’s multi-platform network. 
• Own the sales process end-to-end. Run a disciplined motion from prospecting through close to renewal: pipeline, deal review, pricing, negotiation, and handoff.
• Lead from the front. Bring an active network of advertiser and agency relationships and use it - opening doors, carrying the City Cast story into priority pitches, and personally closing strategic business alongside the team.
• Translate strategy into execution across local, regional, and national. Partner with the CCO on strategy and operationalize distinct motions across single-market, regional, and national buys.
• Lead, coach, and elevate the team. Bring out the best in our existing distributed sales team through hands-on coaching, mentorship, and clear expectations. Cultivate a high-performance culture where top performers grow their careers here.
• Drive forecasting and budgeting rigor. Own weekly pacing, monthly and quarterly forecasts, annual budgeting, and pipeline health.
• Operationalize the sales playbook. Refine the packaging, pricing, pitch narrative, and collateral that wins business.
• Partner across the org to level up what we sell. Work closely with client success, ad ops, and marketing to evolve and maximize product offerings.
• Own key relationships. Lead executive-level relationships with priority advertisers, holding companies, and agency partners, and serve as the escalation point on top accounts.
• Read the market and modernize the org. Track competitive activity and category trends, surface intel to the CCO, and own CRM discipline, sales tooling, and responsible AI adoption.
• Show up in our markets. Travel to City Cast markets throughout the year to build relationships with local sellers and partners. Expected travel is approximately 20% (subject to change).

• 10+ years of digital media sales experience with a proven track record of revenue growth.
• 5+ years of sales management experience, including managing teams remotely across multiple geographies.
• Multi-market or network sales experience. You understand how regional and multi-market deals differ from single-market.
• Audio, podcast, and/or video sales experience, including host-read and integrated sponsorship, programmatic and direct-sold inventory, and attribution.
• Demonstrated success operationalizing go-to-market strategies. Turning strategy into a working sales motion with playbooks, packaging, pricing, and pitch materials.
• A storyteller's instinct. You sell on narrative as much as numbers and know how to make a brand see itself in the network.
• Strong forecasting and budgeting discipline, with deep CRM and sales operations fluency.
• An early adopter of AI in sales work. You actively use AI tools to sharpen your own output and integrate them across the team's workflow, including prospecting, research, pitch prep, and deal coaching.
• A developer of top talent. You've coached and promoted strong performers into bigger roles, and people you've managed seek you out for their next chapter.
• A hands-on operator with an active network. You bring advertiser, brand, and agency relationships you can put to work driving revenue on day one.
• Entrepreneurial, accountable, and results-driven, energized by fast-moving environments and ownership of the outcome.

The starting base salary for this role is $140,000–$160,000, dependent on factors including location, experience, and skills. Total compensation also includes a competitive performance-based bonus tied to revenue outcomes, along with a full benefits package, including a pension. This is a remote position with ~20% travel.

City Cast is an equal opportunity employer committed to excellence through diversity, which involves attracting talented people from diverse backgrounds and traditions. Read about our mission and core values here. We encourage everyone to apply.

About City Cast: We’re a network of one-of-a-kind, daily local news podcasts in cities around the country, accompanied by daily email newsletters, social channels, and websites that keep you in the know about what’s happening in your community. Currently available in Austin, Chicago, DC, Denver, Las Vegas, Madison, Nashville, Philadelphia, Pittsburgh, Portland, Salt Lake, Seattle, and Twin Cities, City Cast is the smartest, easiest way to connect with the place you live and love.

City Cast is an affiliate of Graham Holdings. Read the Graham Holdings Company California Worker Privacy Statement here.