SENIOR DIGITAL SALES EXECUTIVE (REMOTE/USA) - KSLA (GDM - GRAY MEDIA GROUP)

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<strong>Salary/Wage:</strong><br/><br/>$80,000 - $100,000/yr. (Base Salary + Commission + Bonus) (Estimated earnings of $350,000 at budget)<br/><br/><strong>Shift and Schedule:</strong><br/><br/>TBD<br/><br/><strong>Job Type:</strong><br/><br/>Full-Time<br/><br/><strong>Job Summary/Description:</strong><br/><br/>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.<br/><br/>This role is remote, with quarterly travel to your in-market or home market for leadership meetings and planning.<br/><br/>You will own the full sales cycle: prospecting, discovery, solution design with internal specialists, proposal, negotiation, collections, and long-term account growth.<br/><br/>Ideal candidates will reside in/near one of the following locations: Little Rock, AR; Colorado Springs or Denver, CO; Orlando, FL; Minneapolis, MN; Austin, Dallas, or Houston, TX.<br/><br/>Duties/Responsibilities include, but are not limited to:<br/><br/>Unlike commoditized digital ad networks, Gray Digital Media offers sophisticated, high-value solutions that command premium pricing. This means higher commissions, larger deal sizes, and the satisfaction of selling truly differentiated products that deliver measurable ROI to clients. GDM has many resources to help support and grow your campaigns.<br/><br/><strong>What You'll Do:</strong><br/><br/>1. Build and execute a prospecting plan to generate net-new revenue and pipeline (outbound-first)<br/>2. Run high-quality discovery to understand business goals, funnel performance, competitive context, and success metrics<br/>3. Sell integrated digital advertising solutions (as appropriate): <br/> - Paid search / SEM, paid social, programmatic/OTT/CTV, display/video, YouTube, retargeting<br/> - SEO/local search, website/landing page strategy, analytics/measurement, conversion optimization<br/> - Audience strategy, creative approach, and performance reporting<br/>4. Develop multi-product proposals tied to business outcomes (leads, sales, ROAS, CAC/LTV, foot traffic, brand lift, etc.)<br/>5. Partner with internal teams (digital strategists, ad ops, creative, analytics) to scope, launch, optimize, and retain accounts<br/>6. Maintain accurate CRM hygiene, pipeline coverage, and forecast calls<br/>7. Expand existing accounts through performance reviews, upsells, cross-sells, and renewals<br/><br/><strong>What Success Looks Like:</strong><br/><br/><strong>In the first 30-60 days:</strong><br/>- Master Gray Digital Media's offerings, pricing/packaging, and process<br/>- Establish weekly outbound habits and a target account list<br/>- Build a qualified pipeline plan aligned to quota pacing<br/><br/><strong>In 90 days:</strong><br/>- Consistent meeting creation from outbound + referrals<br/>- Active opportunities with clear next steps, stakeholders, and timelines<br/>- Strong internal collaboration and clean CRM execution<br/><br/><strong>In 6-12 months:</strong><br/>- Sustained performance against a $2.5M annual quota<br/>- High client retention and measurable campaign outcomes<br/>- Predictable pipeline generation and forecast accuracy<br/><br/><strong>Qualifications/Requirements:</strong><br/><br/>- Proven success selling digital advertising solutions with meaningful quota responsibility<br/>- Demonstrated ability to generate net-new business (outbound prospecting and account targeting)<br/>- Experience running discovery and selling to outcomes (not just impressions/clicks)<br/>- Comfortable selling across stakeholders (Owner/GM, Marketing Director, CFO/Finance, Operations, etc.)<br/>- Strong presentation, proposal, and negotiation skills<br/>- High comfort with CRM rigor, pipeline management, and forecasting<br/>- Willingness to travel quarterly for in-market/home-market leadership visits<br/><br/><strong>Preferred Qualifications:</strong><br/><br/>- Experience with multi-channel performance programs (SEM + paid social + programmatic/CTV + measurement)<br/>- Track record selling to mid-market and enterprise accounts<br/>- Familiarity with modern measurement approaches (conversion APIs, offline conversions, attribution basics)<br/>- Strong understanding of creative performance drivers and testing<br/><br/>If you feel you're qualified and want to work with a great group of people, go to you may type in the job title, station call letters, or click on <strong>"apply now"</strong>, upload your resume, cover letter, and references<br/><br/>(Current employees who are interested in this position can apply through the <strong>Gray-TV UltiPro self-service portal</strong>)<br/><br/>KSLA-TV/Gray Media is a drug-free company<br/>

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...