Role Description
We're hiring a seasoned, consultative Senior Digital Sales Executive who thrives in a primarily outbound environment and can consistently deliver against a $2.5M annual quota. This role is remote, with quarterly travel to your in-market or home market for leadership meetings and planning. You will own the full sales cycle: prospecting, discovery, solution design with internal specialists, proposal, negotiation, collections, and long-term account growth.
Ideal candidates will reside in/near one of the following locations:
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Little Rock, AR
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Colorado Springs or Denver, CO
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Orlando, FL
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Minneapolis, MN
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Austin, Dallas, or Houston, TX
Duties/Responsibilities include, but are not limited to:
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Build and execute a prospecting plan to generate net-new revenue and pipeline (outbound-first)
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Run high-quality discovery to understand business goals, funnel performance, competitive context, and success metrics
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Sell integrated digital advertising solutions (as appropriate):
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Paid search / SEM, paid social, programmatic/OTT/CTV, display/video, YouTube, retargeting
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SEO/local search, website/landing page strategy, analytics/measurement, conversion optimization
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Audience strategy, creative approach, and performance reporting
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Develop multi-product proposals tied to business outcomes (leads, sales, ROAS, CAC/LTV, foot traffic, brand lift, etc.)
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Partner with internal teams (digital strategists, ad ops, creative, analytics) to scope, launch, optimize, and retain accounts
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Maintain accurate CRM hygiene, pipeline coverage, and forecast calls
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Expand existing accounts through performance reviews, upsells, cross-sells, and renewals
What Success Looks Like:
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In the first 30β60 days:
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Master Gray Digital Media's offerings, pricing/packaging, and process
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Establish weekly outbound habits and a target account list
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Build a qualified pipeline plan aligned to quota pacing
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In 90 days:
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Consistent meeting creation from outbound + referrals
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Active opportunities with clear next steps, stakeholders, and timelines
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Strong internal collaboration and clean CRM execution
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In 6β12 months:
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Sustained performance against a $2.5M annual quota
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High client retention and measurable campaign outcomes
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Predictable pipeline generation and forecast accuracy
Qualifications
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Proven success selling digital advertising solutions with meaningful quota responsibility
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Demonstrated ability to generate net-new business (outbound prospecting and account targeting)
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Experience running discovery and selling to outcomes (not just impressions/clicks)
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Comfortable selling across stakeholders (Owner/GM, Marketing Director, CFO/Finance, Operations, etc.)
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Strong presentation, proposal, and negotiation skills
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High comfort with CRM rigor, pipeline management, and forecasting
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Willingness to travel quarterly for in-market/home-market leadership visits
Preferred Qualifications
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Experience with multi-channel performance programs (SEM + paid social + programmatic/CTV + measurement)
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Track record selling to mid-market and enterprise accounts
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Familiarity with modern measurement approaches (conversion APIs, offline conversions, attribution basics)
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Strong understanding of creative performance drivers and testing
Benefits
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Comprehensive Medical(Rx), Dental, and Vision Coverage
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Health Savings Account with Company contributions
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Flexible Spending Account
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Employer-paid life and disability benefits
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Paid parental leave benefits
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Adoption and Surrogacy Benefits
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401(k) Plan, including matching and profit-sharing contributions
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Employee Assistance Program
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Voluntary benefits, including Hospital Indemnity, Critical Illness, Accident Insurance, and supplemental life insurance coverage
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Paid Time Off, including Relocation PTO
Salary/Wage
$80,000 - $100,000/yr. (Base Salary + Commission + Bonus) (Estimated earnings of $350,000 at budget)
Shift and Schedule
TBD
Job Type
Full-Time