Sales Representative (DMSI)

Location: US-Remote
(AL,AZ,CA,CO,CT,DC,FL,GA,ID,IL,IN,MA,MD,MI,MO,NC,NH,NJ,NV,NY,OH,OR,PA,RI,TN,TX,UT,VA,WA,WI)

Type: Full-Time, Salary, Exempt 

About DMS

Digital Media Solutions (DMS) is a leading provider of technology-enabled digital performance advertising solutions connecting consumers and advertisers. Our platforms support high-volume customer acquisition across multiple industries.

About the Role

We are looking for a Sales Representative to own the full sales cycle — from identifying and engaging prospective insurance agents to closing new business. In this role, you will prospect, qualify, and convert insurance agents into clients through consultative selling and persistent follow-through.

Your success will be measured by closed revenue, activity volume, and contribution to overall pipeline growth.

The ideal candidate is energetic, resilient, and comfortable working in a fast-paced, high-volume environment where you control your own results.

Why Join DMS?

At DMS, you’ll be part of a high-performing, fast-paced sales environment where your effort directly drives your success. You'll develop deep industry knowledge and the full-cycle sales expertise that opens doors throughout your career.

With uncapped commission, clear performance expectations, and a defined path to advancement, this role rewards hustle, consistency, and results. If you're competitive, coachable, and motivated to grow, you'll have every opportunity to shine.

Key Responsibilities

Outbound Prospecting

• Conduct high-volume cold calls, emails, and other outbound outreach to prospective agents..
• Identify and research target accounts and key decision-makers
• Generate interest and initiate conversations with new prospects

Discovery & Qualification

• Lead effective discovery conversations to understand each agent's needs, budget, and fit.
• Ask strategic questions to assess opportunity potential and build rapport.
• Advance qualified prospects through the sales process with a clear path to close.

Closing New Business

• Own deals end-to-end — from first contact through initial deposit. 
• Deliver compelling pitches tailored to each agent's goals and challenges.
• Meet or exceed monthly targets and activity benchmarks.

Pipeline Management

• Maintain a consistent and healthy pipeline of active opportunities.
• Prioritize and manage multiple prospects at various stages simultaneously.
• Keep a steady flow of new prospects entering the funnel.

CRM & Activity Tracking

• Accurately log all outreach, activities, and deal status in CRM (e.g., Salesforce).
• Keep prospect and account data current and organized.
• Track personal performance against activity, pipeline, and revenue goals.

Follow- Up & Relationship Building

• Execute timely, multi-touch follow-up strategies to move deals forward.
• Build trust and credibility with prospects throughout the buying process.
• Maintain professional, persistent, and personalized communication at every stage.

• 0–2 years of experience in sales, business development, or a related field
• High school diploma or GED required; Bachelor’s degree preferred

Skills:

• Strong written, verbal, and interpersonal communication skills
• Comfortable making cold calls and handling rejection
• Ability to manage high activity levels and stay organized
• Proficiency in Microsoft Office Suite (Excel, Outlook, Word, etc.)

Preferred Qualifications:

• Inside sales experience with a track record of exceeding quota achievement.
• Experience with high-volume cold calling and outbound prospecting.
• Skilled at writing effective cold outreach emails.
• Familiarity with Salesforce or similar CRM tools.
• Understanding of sales activity metrics and revenue forecasting.
• Experience selling to or working within the insurance industry (a plus).

Compensation: The starting hourly rate for this position is $21.64-$23 per hour (based on experience) + uncapped commission.