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Entry Level Remote Helpdesk Jobs in Chicago, IL (NOW HIRING)

Nexera

Entry Level Remote Sales Role

Chicago, IL · Remote

$1.5K - $5.3K/wk

About this role We are hiring entry-level Financial Sales Consultants to join our remote team ... In this role, you will help families find the right financial protection coverage for their needs ...

Nexera

Entry Level Remote Insurance Sales

Chicago, IL · Remote

$1.5K - $3.2K/wk

About this role We're hiring entry-level Financial Sales Consultants for our remote team ... You'll help families find the right financial protection for their needs -- by phone and Zoom, from ...

Nexera

Entry Level Remote Insurance Sales

Chicago, IL · Remote

$1.5K - $3.2K/wk

About this role We're hiring entry-level Financial Sales Consultants for our remote team ... You'll help families find the right financial protection for their needs -- by phone and Zoom, from ...

AO Globe Life

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Entry Level Sales Associate (Remote)

Chicago, IL · Remote

$60K - $80K/yr

Entry Level Sales Associate (Remote) 100% Remote | Full-Time | United States & Canada Location ... Help clients understand the choices available to them * Assist clients with the next steps when ...

Posted today

AO Globe Life

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Remote Client Account Representative (Entry Level)

Chicago, IL · Remote

$60K - $80K/yr

Help qualified clients complete the enrollment process * Keep client information and appointment details organized * Attend online training and team meetings What Makes This a Sales Position? You'll ...

Posted today

Inizio Evoke

Associate Project Manager

Chicago, IL · Remote

$58K - $65K/yr

This is an entry-level remote role. You Will: * Help to keep projects moving through the agency, which includes routing work for review according to internal and external processes, handling ...

Globe Life: Icaza Jammoul Organization

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Entry-Level Sales Representative | 100% Remote

Chicago, IL · Remote

$52K - $65K/yr

Entry-Level Sales Representative (Open to Applicants residing in Chicago, IL and surrounding areas ... In this Sales Representative position, you will help grow our branch, Icaza Jammoul Organization by ...

Globe Life Insurance

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Remote Customer Sales and Support Representative (Entry-Level)

Chicago, IL · Remote

$60K - $80K/yr

Remote Customer Sales and Support Representative (Entry-Level) 100% Remote | United States & Canada ... At AO Globe Life , we're looking for individuals who are eager to learn, enjoy helping people, and ...

Globe Life Insurance

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Remote Customer Sales and Support Representative (Entry-Level)

Chicago, IL · Remote

$60K - $80K/yr

Remote Customer Sales and Support Representative (Entry-Level) 100% Remote | United States & Canada ... At AO Globe Life , we're looking for individuals who are eager to learn, enjoy helping people, and ...

Globe Life Insurance

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Remote Customer Sales and Support Representative (Entry-Level)

Chicago, IL · Remote

$60K - $80K/yr

Remote Customer Sales and Support Representative (Entry-Level) 100% Remote | United States & Canada ... At AO Globe Life , we're looking for individuals who are eager to learn, enjoy helping people, and ...

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Entry Level Remote Helpdesk information

See Chicago, IL salary details

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$23

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How much do entry level remote helpdesk jobs pay per hour?

As of Aug 10, 2026, the average hourly pay for entry level remote helpdesk in Chicago, IL is $23.85, according to ZipRecruiter salary data. Most workers in this role earn between $19.81 and $26.73 per hour, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive as an entry level remote helpdesk professional?

To thrive as an Entry Level Remote Helpdesk professional, you need a basic understanding of computer systems, troubleshooting skills, and often a relevant certification such as CompTIA A+ or equivalent experience. Familiarity with ticketing systems (like Zendesk or ServiceNow), remote desktop tools, and standard office software is typically required. Excellent communication, patience, and problem-solving abilities help you deliver effective support and build trust with users. These skills are crucial because they enable you to resolve technical issues efficiently while maintaining customer satisfaction from a remote environment.

What is an entry level remote helpdesk?

An entry level remote helpdesk job involves providing technical support and assistance to customers or employees, usually through phone, email, or chat, while working from a remote location. Responsibilities typically include troubleshooting common computer or software issues, answering user inquiries, and escalating more complex problems to higher-level technicians. These positions are ideal for individuals starting their IT careers and often require good communication skills, basic technical knowledge, and the ability to work independently. Entry level remote helpdesk roles can offer valuable experience and a pathway to more advanced positions within IT support.

What is the difference between Entry Level Remote Helpdesk vs Technical Support Specialist?

AspectEntry Level Remote HelpdeskTechnical Support Specialist
CertificationsBasic certifications like CompTIA A+ often preferredSimilar certifications, sometimes more advanced or specialized
Work EnvironmentRemote, customer-facing, troubleshooting via phone or chatRemote or on-site, troubleshooting hardware/software issues
Industry UsageCommon in IT, tech support, customer service sectorsUsed across IT, software, hardware, and network support roles

Both roles involve technical troubleshooting and customer support, often requiring similar certifications. The main difference lies in the scope: Entry Level Remote Helpdesk typically handles basic issues and customer inquiries remotely, while Technical Support Specialists may deal with more complex technical problems, sometimes on-site. Understanding these distinctions helps job seekers target the right roles based on their skills and career goals.

What are some common challenges faced by entry level remote helpdesk professionals, and how can they be addressed?

Entry level remote helpdesk professionals often encounter challenges such as troubleshooting technical issues without in-person context, managing multiple support tickets simultaneously, and communicating clearly with users who have varying levels of technical knowledge. To address these challenges, it's important to develop strong written and verbal communication skills, stay organized with ticketing systems, and actively participate in team chats or meetings to share solutions and learn from more experienced colleagues. Many organizations provide ongoing training and mentorship, so taking advantage of these resources can also help you adapt and grow in the role.
What are the most commonly searched types of Remote Helpdesk jobs in Chicago, IL? The most popular types of Remote Helpdesk jobs in Chicago, IL are:
What are popular job titles related to Entry Level Remote Helpdesk jobs in Chicago, IL? For Entry Level Remote Helpdesk jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching Entry Level Remote Helpdesk jobs in Chicago, IL look for? The top searched job categories for Entry Level Remote Helpdesk jobs in Chicago, IL are:
What cities near Chicago, IL are hiring for Entry Level Remote Helpdesk jobs? Cities near Chicago, IL with the most Entry Level Remote Helpdesk job openings:
Entry Level Remote Helpdesk jobs near you
Infographic showing various Entry Level Remote Helpdesk job openings in Chicago, IL as of August 2026, with employment types broken down into 79% Full Time, and 21% Part Time. Highlights an 100% Remote job distribution, with an average salary of $49,605 per year, or $23.8 per hour.

Entry Level Sales Representative - Remote | 80K + | Training Provided | Inhouse leads

Meron & Kemboi Financial Agency

Chicago, IL • Remote

$3.5K - $5.5K/wk

Full-time

Posted 20 days ago

Job description

We are currently expanding and looking for motivated individuals to join our team in an entry-level remote sales position.

No prior experience is required. We provide full training, mentorship, and a proven system to help you succeed from day one.

This is a work-from-home opportunity where you will be speaking with clients who have already requested information about life insurance coverage. There is no cold calling involved.

What you’ll be doing:
• Following up with warm, inbound leads
• Running virtual appointments over phone or Zoom
• Helping clients find coverage that fits their needs
• Learning and applying a proven sales system

Who this is a great fit for:
Entry-level candidates, career changers, customer service reps, teachers, realtors, mortgage professionals, and individuals looking to build a high-income skill set.

What we provide:
• Full training and ongoing mentorship
• Flexible schedule (part-time or full-time)
• Warm leads (no cold calling)
• Proven system designed for beginners
• Opportunity to earn $100K+

Compensation:
This is a 100% commission-based position with uncapped earning potential.
Starting commission begins at 80%, with opportunities for advancement based on performance.

If you are coachable, motivated, and ready to learn a new skill that can change your income, apply today.