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Remote Weekend Helpdesk Jobs in Naperville, IL (NOW HIRING)

Addison Group

Service Desk Analyst

Chicago, IL · Remote

$20 - $25/hr

Rotating weekend coverage approximately every 5 weeks (Saturday 8:00 AM - 5:00 PM and Sunday 11:00 ... remote, and ticket-based channels. The ideal candidate enjoys helping people, excels in a fast ...

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All JobsHelpdesk JobsRemote Weekend Helpdesk JobsRemote Weekend Helpdesk Jobs in Naperville, IL

Remote Weekend Helpdesk information

See Naperville, IL salary details

$12

$23

$33

How much do remote weekend helpdesk jobs pay per hour?

As of Aug 8, 2026, the average hourly pay for remote weekend helpdesk in Naperville, IL is $23.12, according to ZipRecruiter salary data. Most workers in this role earn between $19.18 and $25.91 per hour, depending on experience, location, and employer.

What is the difference between Remote Weekend Helpdesk vs Remote IT Support Specialist?

AspectRemote Weekend HelpdeskRemote IT Support Specialist
CredentialsBasic certifications like CompTIA A+ often preferredMore advanced certifications like Network+ or Security+ may be required
Work EnvironmentRemote, customer service-focused, primarily troubleshootingRemote or on-site, technical problem-solving, network, and hardware support
Employer & IndustryTech companies, MSPs, customer service centersIT departments, tech firms, managed service providers
Search & Comparison IntentPeople seeking weekend tech support rolesIndividuals looking for more technical, ongoing IT support roles

The Remote Weekend Helpdesk typically involves providing basic technical support during weekends, focusing on customer service and troubleshooting. In contrast, a Remote IT Support Specialist often handles more complex technical issues, including network and hardware support, with higher certification requirements. Both roles are remote and industry-related but differ in technical depth and responsibilities.

What are popular job titles related to Remote Weekend Helpdesk jobs in Naperville, IL? For Remote Weekend Helpdesk jobs in Naperville, IL, the most frequently searched job titles are:
What job categories do people searching Remote Weekend Helpdesk jobs in Naperville, IL look for? The top searched job categories for Remote Weekend Helpdesk jobs in Naperville, IL are:
What cities near Naperville, IL are hiring for Remote Weekend Helpdesk jobs? Cities near Naperville, IL with the most Remote Weekend Helpdesk job openings:
Remote Weekend Helpdesk jobs near you
Infographic showing various Remote Weekend Helpdesk job openings in Naperville, IL as of July 2026, with employment types broken down into 3% Locum Tenens, 85% Full Time, 9% Part Time, and 3% Contract. Highlights an 93% Physical, 2% Hybrid, and 5% Remote job distribution, with an average salary of $48,082 per year, or $23.1 per hour.

Sales Director, Chicago, IL

Agile People and Payroll LLC

Chicago, IL • On-site, Remote

$85K/yr

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Posted 25 days ago

Job description

ABOUT AGILITY INSURANCE SERVICES
Agility Insurance Services is a national Field Marketing Organization (FMO) dedicated to helping independent agents and agencies grow their businesses through industry-leading training, carrier partnerships, contracting support, marketing resources, and sales enablement. With a diverse portfolio that includes Medicare, ACA, Life, Supplemental, and Group products, Agility empowers insurance professionals to better serve their clients while expanding their opportunities for success. Our mission is to support agent growth through education, innovation, and personalized partnership, creating lasting value for both agents and the communities they serve.
POSITION SUMMARY
The Sales Director is a visionary leader responsible for driving membership and business growth through agent and agency recruitment, career partnerships, market development, and community engagement. This role drives business development through relationship-building, industry events, community engagement, and innovative growth strategies. The role equips agents with training, tools, technology, and support needed to grow their business across Medicare, ACA, Life, Supplemental, and Group insurance products. You'll help create an environment where collaboration fuels measurable results. If you're energized by connecting people, inspiring growth, and shaping the future of the insurance industry, this role would be ideal for YOU!
Requirements
ROLE RESPONSIBILITIES :
  • Build a year-round sales and recruitment strategy while servicing all agents & agencies to ensure all sales objectives are met /exceeded.
  • Accountable to oversee our community presence and grassroots lead generation efforts.
  • Establish relationships with key partners within each market, educate agents /agencies on Agility Insurance Services' compelling value proposition, growth initiatives and member retention.
  • Responsible for training on products, services, compliance, and building community relationships.
  • Responsible for budgeting and market spending.
  • Effectively communicate both internally and externally
  • Translate complex data into clear and actionable recommendations to drive business.
  • Work hand in hand with our Producer Support Team to ensure utmost agent satisfaction.
  • Ensure CMS, State, and Federal regulatory guidelines are communicated to direct reports and other team members as needed to maintain compliance.
  • Recruiting agents and agencies
  • Drive RTS (Ready to Sell) growth and agent engagement.
  • Establish and retain relationships throughout the market and business.
  • Perform other duties as assigned.

REQUIRED QUALIFICATIONS
  • Three (3) + years of experience in the healthcare or Medicare industry, with a proven track record of managing insurance agents, agency relationships, and driving business growth. Previous broker or agency experience is preferred.
  • College degree preferred.
  • Active Health Insurance License is required.
  • Bilingual in English/Spanish preferred.
  • Demonstrated ability to quickly establish, develop, and maintain strong relationships with agent partners.
  • Strong presentation, interpersonal, and communication skills.
  • Excellent written and verbal communication skills.
  • Knowledge of and ability to effectively present ACA, Medicare, Life, and Ancillary insurance products.
  • Willingness to travel up to 75% within the assigned market, including overnight travel as needed.
  • Proficient in Microsoft Office Suite, particularly Excel, Word, Outlook, and PowerPoint.
  • Must have reliable transportation.
  • Self-motivated with excellent time management and organizational skills.
  • Innovative, results-driven, and focused on achieving growth objectives.
  • Must live in the market area

What We Offer:
Compensation:
  • Base Salary: $85,000.00 annually
  • Additional Compensation: Quarterly performance-based incentive

  • Benefits:

  • 401(k) retirement
  • Medical insurance
  • Dental insurance
  • Vision insurance
  • Life insurance
  • Paid time off (PTO)

  • Travel Requirements:

  • Up to 75%
  • Work Schedule:
  • Monday through Friday
  • Remote
  • Weekend availability as business needs require

If you're a motivated, bilingual professional with a passion for helping others, we want to meet you! Don't miss this exciting opportunity! Apply today and take the next step in YOUR career.
Check us out! www.enrollinsurance.com
Agility Insurance Services LLC provides equal employment opportunities to all applicants, without regard to unlawful considerations of or discrimination against race, religion, creed, color, nationality, sex, sexual orientation, gender identity, age, ancestry, physical or mental disability, medical condition or characteristics, marital status, or any other classification prohibited by applicable local, state, or federal laws. Agility Insurance Services LLC may obtain a 'consumer report' about you from a consumer reporting agency for employment purposes. A 'consumer report' is a background screening report that may contain information regarding your criminal history, driving history, and information about you.

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