Regional Director, Digital Sales (Chicago)

Nexstar Media Group is seeking a Regional Director of Digital Sales responsible for accelerating digital revenue across a defined portfolio of local markets. This senior role is focused on execution—partnering with local leadership to drive performance, increase share of wallet, and close high-value opportunities across owned & operated inventory and marketing services.The ideal candidate has a proven track record in digital ad sales, particularly in the OTT/CTV ecosystem, with experience in programmatic advertising, data-first solutions, audience targeting, and strategic partnership development. This is a high impact role for a revenue leader who thrives in-market, influences outcomes, and holds teams accountable to digital growth targets.Key ResponsibilitiesRevenue Leadership & Sales ExecutionOwn digital revenue outcomes across assigned markets, driving growth across all product lines: OTT/CTV, Display, OLV and Marketing Services.Partner with local GMs, GSMs, and AEs to develop and close high-value deals, expand existing accounts, and penetrate new business.Push adoption of multi-platform solutions that drive measurable ROI for clients and maximize yield on premium inventory.Act as the point of escalation and deal support on key enterprise, regional, and multi-market opportunities.Support Regional Vice Presidents on strategic initiatives and digital growth opportunities for marketsField Enablement & Market ActivationSupport and influence local sales teams to prioritize digital in every sales conversation.Identify underperforming segments and implement targeted actions to accelerate growth.Reinforce the company’s go-to-market strategy, pricing discipline, and product positioning to win share in competitive markets.Help implement quarterly and annual plans that align to local revenue targets and product mix goals.Performance Accountability & ForecastingTrack regional pacing to budget and proactively address shortfalls with market-level interventions.Lead weekly forecast reviews, monthly pipeline health checks, and deal strategy sessions with local sales leadership.Partner with corporate revenue operations to ensure forecast accuracy, CRM discipline, and revenue visibility.Strategic CollaborationShare best practices across regions and contribute to corporate feedback loops on product performance and sales blockers.Support recruitment and onboarding of top-tier digital talent in key markets as needed.KPIs & Success MetricsDigital revenue growth (YoY and pacing to budget)Average deal size and digital product mixShare of wallet growth in top accountsPipeline coverage and close ratesNumber of markets achieving quotaQualifications6+ years in digital media sales or digital revenue leadership, preferably with local/regional media organizationsProven success leading or influencing sales teams to exceed digital revenue goalsDeep expertise across digital ad channels including CTV/OTT, display, programmatic, native, search, social, and emailStrong executive presence and ability to command sales strategy discussions in-marketDemonstrated success in building and closing 7-figure digital deals with major advertisers or agenciesFluent in CRM tools, forecasting methodologies, and digital advertising platformsHighly autonomous and results-driven, with a bias toward actionAbility to travel up to 75%Salary Range: $180,000 - $225,000Job Location: Position can be located in any Nexstar market.SummaryLocation: TX, Irving; CA, Los Angeles; NY, New York; IL, ChicagoType: Full time