Remote Senior Digital Sales Executive - $2.5M Quota

Gray Media; Shreveport (LA); Remote; USD 80,000 - 100,000; Full time

Benefits offered by this job

Medical benefits

HSA

FSA

Life and disability

Job summary

Gray Media is hiring a seasoned Senior Digital Sales Executive who thrives in an outbound environment and can deliver against a $2.5M annual quota. This remote role includes quarterly travel to in-market or home market for leadership meetings and planning.

You will own the full sales cycle—from prospecting and discovery to solution design, proposals, negotiation, and long-term account growth—and reside in/near target markets such as Little Rock, AR; Colorado Springs or Denver, CO; Orlando, FL;

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.

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 (digital strategists, ad ops, creative, analytics) 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 sales

Outbound prospecting

CRM proficiency

Negotiation skills

Tools

CRM systems

Job description

Gray Media is hiring a seasoned Senior Digital Sales Executive who thrives in an outbound environment and can deliver against a $2.5M annual quota. This remote role includes quarterly travel to in-market or home market for leadership meetings and planning.

You will own the full sales cycle—from prospecting and discovery to solution design, proposals, negotiation, and long-term account growth—and reside in/near target markets such as Little Rock, AR; Colorado Springs or Denver, CO; Orlando, FL;