Remote Senior Digital Sales Exec – $2.5M Annual Quota

FOX Carolina News; Oregon; Hybrid; USD 80,000 - 100,000; Full time

Job summary

Gray Media is hiring a seasoned Senior Digital Sales Executive for a remote role with quarterly travel to in-market or home market leadership meetings. You will own the full sales cycle from prospecting through negotiations, targeting a $2.5M annual quota and delivering measurable ROI for clients.

Ideal candidates reside in or near listed markets and bring proven success selling digital advertising solutions with a strong emphasis on outcomes and multi-product proposals.

Qualifications

• Proven success selling digital advertising solutions with meaningful quota responsibility.
• Demonstrated ability to generate net-new business (outbound prospecting and account targeting).
• Experience running discovery and selling to outcomes (not just impressions/clicks).
• Comfortable selling across stakeholders (Owner/GM, Marketing Director, CFO/Finance, Operations, etc.).
• Strong presentation, proposal, and negotiation skills.
• High comfort with CRM rigor, pipeline management, and forecasting.
• Willingness to travel quarterly for in-market/home-market leadership visits.

Responsibilities

• Build and execute a prospecting plan to generate net-new revenue and pipeline (outbound-first).
• Run high-quality discovery to understand business goals, funnel performance, competitive context, and success metrics.
• Sell integrated digital advertising solutions (as appropriate): Paid search/SEM, paid social, programmatic/OTT/CTV, display/video, YouTube, retargeting.
• Develop multi-product proposals tied to business outcomes (leads, sales, ROAS, CAC/LTV, foot traffic, brand lift).
• Partner with internal teams to scope, launch, optimize, and retain accounts.
• Maintain accurate CRM hygiene, pipeline coverage, and forecast calls.
• Expand existing accounts through performance reviews, upsells, cross-sells, and renewals.

Skills

Digital advertising

Outbound sales

CRM mastery

Negotiation

Tools

CRM

Job description

Gray Media is hiring a seasoned Senior Digital Sales Executive for a remote role with quarterly travel to in-market or home market leadership meetings. You will own the full sales cycle from prospecting through negotiations, targeting a $2.5M annual quota and delivering measurable ROI for clients.

Ideal candidates reside in or near listed markets and bring proven success selling digital advertising solutions with a strong emphasis on outcomes and multi-product proposals.