Senior Digital Sales Executive

Gray Media

. Build and execute an outbound-first prospecting plan to generate net-new revenue and pipeline .

Posted 10/30/2026full-timeRemote • United StatesSenior💰 $80,000 - $100,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in selling integrated digital advertising solutions, managing the full sales cycle, and achieving significant revenue targets. Proficient in outbound prospecting, account management, and collaborating with cross-functional teams to drive business outcomes.

Highest-signal resume keywords

Digital Advertising Solutions SalesOutbound ProspectingCRM ManagementProposal DevelopmentAccount Growth

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Paid Search/SEMPaid SocialProgrammatic/OTT/CTVSEO/Local SearchAnalytics/MeasurementConversion OptimizationAudience StrategyPerformance ReportingMulti-Product ProposalsForecasting

Soft Skills

Presentation SkillsNegotiation SkillsCollaborationCommunication

Tools & Technologies

CRM Software

Industry Keywords

Net-New RevenueFunnel PerformanceROASCAC/LTVFoot TrafficBrand LiftStakeholder EngagementPerformance ReviewsUpsellingCross-Selling

About the role

Key responsibilities & impact

Build and execute an outbound-first prospecting plan to generate net-new revenue and pipeline
Conduct discovery to understand business goals, funnel performance, competitive context, and success metrics
Sell integrated digital advertising solutions including paid search/SEM, paid social, programmatic/OTT/CTV, display/video, YouTube, retargeting, SEO/local search, website/landing page strategy, analytics/measurement, conversion optimization, audience strategy, creative approach, and performance reporting
Develop multi-product proposals tied to outcomes such as leads, sales, ROAS, CAC/LTV, foot traffic, and brand lift
Partner with digital strategists, ad operations, creative, and analytics teams to scope, launch, optimize, and retain accounts
Maintain CRM hygiene, pipeline coverage, and forecast calls
Expand existing accounts through performance reviews, upsells, cross-sells, and renewals
Deliver against a $2.5M annual quota
Own the full sales cycle from prospecting and discovery through solution design, proposal, negotiation, collections, and long-term account growth

Requirements

What you’ll need

Proven success selling digital advertising solutions with meaningful quota responsibility
Demonstrated ability to generate net-new business through outbound prospecting and account targeting
Experience running discovery and selling to outcomes, not just impressions/clicks
Comfortable selling across stakeholders including Owner/GM, Marketing Director, CFO/Finance, and Operations
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
Preferred: Experience with multi-channel performance programs including SEM, paid social, programmatic/CTV, and measurement
Preferred: Track record selling to mid-market and enterprise accounts
Preferred: Familiarity with conversion APIs, offline conversions, and attribution basics
Preferred: Strong understanding of creative performance drivers and testing

Benefits

Comp & perks

Comprehensive Medical(Rx), Dental, and Vision Coverage
Health Savings Account with Company contributions
Flexible Spending Account
Employer-paid life and disability benefits
Paid parental leave benefits
Adoption and Surrogacy Benefits
401(k) Plan, including matching and profit-sharing contributions
Employee Assistance Program
Voluntary benefits, including Hospital Indemnity, Critical Illness, Accident Insurance, and supplemental life insurance coverage
Paid Time Off, including Relocation PTO