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Entry Level Remote Sales Development Representative Jobs in Winchester, VA

HMG Careers

Remote Sales Representative

Middletown, VA · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work ...

HMG Careers

Remote Sales Representative

Paw Paw, WV · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work ...

HMG Careers

Remote Sales Representative

Inwood, WV · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work ...

HMG Careers

Remote Sales Representative

Berryville, VA · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work ...

HMG Careers

Remote Sales Representative

Maurertown, VA · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work ...

HMG Careers

Remote Sales Representative

Winchester, VA · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work ...

HMG Careers

Remote Sales Representative

Gore, VA · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work ...

HMG Careers

Remote Sales Representative

Upperville, VA · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work ...

HMG Careers

Remote Sales Representative

Hillsboro, VA · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work ...

HMG Careers

Remote Sales Representative

Front Royal, VA · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work ...

HMG Careers

Remote Sales Representative

Martinsburg, WV · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work ...

HMG Careers

Remote Sales Representative

Paris, VA · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work ...

HMG Careers

Remote Sales Representative

Hayfield, VA · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work ...

HMG Careers

Remote Sales Representative

Marshall, VA · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work ...

HMG Careers

Remote Sales Representative

Chester Gap, VA · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work ...

HMG Careers

Remote Sales Representative

Charles Town, WV · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work ...

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Showing results 1-20

All JobsSales Development Representative JobsEntry Level Remote Sales Development Representative JobsEntry Level Remote Sales Development Representative Jobs in Winchester, VA

Entry Level Remote Sales Development Representative information

See Winchester, VA salary details

$28.2K

$61.6K

$97.2K

How much do entry level remote sales development representative jobs pay per year?

As of Aug 18, 2026, the average yearly pay for entry level remote sales development representative in Winchester, VA is $61,645.00, according to ZipRecruiter salary data. Most workers in this role earn between $45,700.00 and $73,400.00 per year, depending on experience, location, and employer.

What is an entry level remote sales development representative?

An Entry Level Remote Sales Development Representative (SDR) is a professional who works from a remote location to identify and qualify potential sales leads for a company. Their main responsibilities typically include researching prospective clients, reaching out via email or phone, and setting up meetings for more senior sales staff. This role is often the first step in a sales career, requiring strong communication skills and the ability to learn quickly. Entry level SDRs are usually provided with training and support to help them succeed and progress within the organization.

What are the key skills and qualifications needed to thrive as an entry level remote sales development representative?

To thrive as an Entry Level Remote Sales Development Representative, you generally need strong communication skills, a results-driven mindset, and a bachelor's degree, although some positions may accept relevant experience in lieu of formal education. Familiarity with CRM software such as Salesforce, LinkedIn Sales Navigator, and sales engagement tools is typically expected. Persistence, adaptability, and excellent time management are standout soft skills in this role. These skills and qualifications are crucial for effectively generating leads, building relationships remotely, and driving sales pipeline growth from a virtual setting.

What are some typical challenges faced by entry level remote sales development representatives and how can they be addressed?

Entry Level Remote Sales Development Representatives often face challenges such as maintaining motivation in a virtual environment, managing rejection from prospects, and building rapport without in-person interactions. To address these, it's important to establish a structured daily routine, regularly check in with your team for support, and leverage available sales enablement tools. Many companies offer mentorship programs and virtual training sessions to help new reps develop effective outreach strategies and improve communication skills. Staying proactive in seeking feedback and celebrating small wins can help build confidence and resilience in this role.

What is the difference between Entry Level Remote Sales Development Representative vs Inside Sales Representative?

AspectEntry Level Remote Sales Development RepresentativeInside Sales Representative
Primary RoleGenerate leads and qualify prospects remotelyClose sales and manage client accounts remotely
Required SkillsCommunication, prospecting, CRM familiarityNegotiation, closing, relationship management
Work EnvironmentRemote, often entry-levelRemote or office-based, more experienced
Typical CertificationsNone required, often on-the-job trainingSales certifications beneficial

While both roles involve remote sales activities, the Entry Level Remote Sales Development Representative focuses on lead generation and qualification, whereas the Inside Sales Representative handles closing deals and managing client relationships. The former is ideal for those starting in sales, while the latter requires more experience in sales processes.

What are popular job titles related to Entry Level Remote Sales Development Representative jobs in Winchester, VA?

For Entry Level Remote Sales Development Representative jobs in Winchester, VA, the most frequently searched job titles are:

What job categories do people searching Entry Level Remote Sales Development Representative jobs in Winchester, VA look for?

The top searched job categories for Entry Level Remote Sales Development Representative jobs in Winchester, VA are:

What cities near Winchester, VA are hiring for Entry Level Remote Sales Development Representative jobs?

Cities near Winchester, VA with the most Entry Level Remote Sales Development Representative job openings:

Entry Level Remote Sales Development Representative jobs near you
Infographic showing various Entry Level Remote Sales Development Representative job openings in Winchester, VA as of August 2026, with employment types broken down into 50% Full Time, and 50% Part Time. Highlights an 100% Remote job distribution, with an average salary of $61,645 per year, or $29.6 per hour.

Entry Level Remote Sales (Training + Mentorship Provided)

The Semler Agency

Winchester, VA • On-site, Remote

Part-time

Re-posted 9 days ago

Job description

We are hiring for an entry-level remote sales position with full training and mentorship provided.
This is a work-from-home opportunity where you will learn how to help families secure life insurance coverage while building your own income.
No prior experience is required. We are looking for individuals who are:
  • Coachable
  • Reliable
  • Willing to follow a proven system
What You'll Do:
  • Speak with individuals who have requested information
  • Help them understand coverage options
  • Work within a structured training environment
What We Provide:
  • Step-by-step training
  • Ongoing mentorship
  • Flexible schedule
  • Remote work environment

After applying, you will receive an email with next steps to schedule a quick overview call. Please keep an eye out for a text from 240-301-1401 after applying.
*NOTE: Equal opportunity, not equal outcome. No agent's success, earnings, or production results should be viewed as typical, average or expected. Not all agents achieve the same or similar results, and no particular results are guaranteed. Your level of success will be determined by several factors, including the amount of work you put in, your ability to successfully follow and implement our training and sales system and engage with our lead system, and the Insurance needs of the customers in the geographic areas in which you choose to work.

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