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Remote Entry Level Leadership Jobs in Chicago, IL

AO Globe Life

Remote- Entry Level Manager

Chicago, IL · On-site +1

  • Medical

Are you ready to revolutionize sales from the comfort of your own home? We're seeking exceptional leaders to join our remote team and take charge of our customer experience revolution! The ...

AO Globe Life

Remote- Entry Level Manager

Chicago, IL · On-site +1

  • Medical

Are you ready to revolutionize sales from the comfort of your own home? We're seeking exceptional leaders to join our remote team and take charge of our customer experience revolution! The ...

AO Globe Life

Remote- Entry Level Manager

Chicago, IL · On-site +1

  • Medical

Are you ready to revolutionize sales from the comfort of your own home? We're seeking exceptional leaders to join our remote team and take charge of our customer experience revolution! The ...

AO Globe Life

Remote- Entry Level Manager

Chicago, IL · On-site +1

  • Medical

Are you ready to revolutionize sales from the comfort of your own home? We're seeking exceptional leaders to join our remote team and take charge of our customer experience revolution! The ...

AO Globe Life

Remote- Entry Level Manager

Chicago, IL · On-site +1

  • Medical

Are you ready to revolutionize sales from the comfort of your own home? We're seeking exceptional leaders to join our remote team and take charge of our customer experience revolution! The ...

Stratford Davis

Remote Inside Sales Representative

Chicago, IL · Remote

$85K - $150K/yr

  • Medical

  • Dental

  • Vision

  • Life

Join our team as a Remote Entry Level Sales Representative and help everyday families secure their ... Step-by-step guidance from senior industry leaders. * Benefits Options: Access to healthcare ...

Nexera

Entry Level Remote Sales Role

Chicago, IL · Remote

$1.5K - $5.3K/wk

Contact warm inbound leads -- people who have already requested information about protecting their families financially * Conduct phone and Zoom consultations to understand each client's needs and ...

AO Globe Life

Be Seen First

Remote Client Account Representative (Entry Level)

Chicago, IL · Remote

$60K - $80K/yr

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

Remote Client Account Representative (Entry Level) 100% Remote | Full-Time | United States & Canada ... Client appointments and leads provided * No cold calling * Sales and product training * Ongoing ...

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 ... Contacting warm inbound leads -- people who've already asked for help protecting their families

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 ... Contacting warm inbound leads -- people who've already asked for help protecting their families

Globe Life: Icaza Jammoul Organization

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Entry-Level Sales Representative | 100% Remote

Evanston, IL · Remote

$52K - $65K/yr

  • Medical

  • Life

  • Retirement

Entry-Level Sales Representative (Open to Applicants residing in Evanston, IL and surrounding areas ... Life is a leading insurance and supplemental benefits provider. In this Sales Representative ...

New

Globe Life Insurance

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Entry Level Customer Sales Representative (100% Remote)

Aurora, IL · Remote

$60K - $80K/yr

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

Entry Level Customer Sales Representative (100% Remote) Remote | United States & Canada ... Qualified leads -- connect with people who have requested information * Structured training ...

Globe Life Insurance

Be Seen First

Entry Level Customer Sales Representative (100% Remote)

Joliet, IL · Remote

$60K - $80K/yr

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

Entry Level Customer Sales Representative (100% Remote) Remote | United States & Canada ... Qualified leads -- connect with people who have requested information * Structured training ...

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Showing results 1-20

All JobsLeadership JobsRemote Entry Level Leadership JobsRemote Entry Level Leadership Jobs in Chicago, IL

Remote Entry Level Leadership information

See Chicago, IL salary details

$14

$27

$81

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

As of Aug 13, 2026, the average hourly pay for remote entry level leadership in Chicago, IL is $27.53, according to ZipRecruiter salary data. Most workers in this role earn between $17.60 and $23.75 per hour, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive as a remote entry level leader?

To thrive as a Remote Entry Level Leader, you need foundational leadership skills, basic project management knowledge, and at least a bachelor’s degree in a relevant field. Familiarity with collaboration tools like Slack, project management platforms such as Asana or Trello, and video conferencing software is often required. Strong communication, time management, and self-motivation are crucial soft skills for effectively guiding remote teams. These abilities are essential for maintaining productivity, fostering team engagement, and achieving organizational goals in a distributed work environment.

What is the difference between Remote Entry Level Leadership vs Remote Customer Service Supervisor?

AspectRemote Entry Level LeadershipRemote Customer Service Supervisor
Required CredentialsHigh school diploma or equivalent; leadership potentialHigh school diploma; customer service experience
Work EnvironmentVirtual team management, project coordinationOverseeing customer support teams remotely
Industry UsageVarious industries including retail, tech, healthcarePrimarily retail, telecom, and service sectors
Common Search IntentEntry-level leadership roles with remote optionsSupervisory roles in customer service teams remotely

Remote Entry Level Leadership and Remote Customer Service Supervisor roles both involve overseeing teams remotely, but the former emphasizes leadership development and project management, while the latter focuses on managing customer support operations. Both roles typically require strong communication skills and basic leadership qualities, making them popular choices for those starting in management positions in a remote setting.

What is a remote entry level leadership position?

A Remote Entry Level Leadership position is a job designed for individuals who are new to management and are responsible for leading small teams or projects while working from a remote location. These roles typically provide training and mentorship to help employees develop essential leadership and communication skills. While the responsibilities may vary by industry, common tasks include coordinating team activities, monitoring progress, and supporting team members' growth. This type of position is ideal for those who want to start a career in management while enjoying the flexibility of remote work.

What types of support and training can remote entry level leadership roles expect when starting out?

Remote entry level leadership roles typically offer structured onboarding programs, mentorship opportunities, and regular check-ins with supervisors to help you acclimate to both the company culture and your new responsibilities. You can expect to participate in virtual training sessions focused on communication, team management, and project coordination. Collaboration tools like Slack, Zoom, or Microsoft Teams are commonly used for team interaction and support. Many organizations also provide access to leadership development resources and peer groups to help you build confidence and grow your skills remotely.

What are the most commonly searched types of Remote Leadership jobs in Chicago, IL?

The most popular types of Remote Leadership jobs in Chicago, IL are:

What are popular job titles related to Remote Entry Level Leadership jobs in Chicago, IL?

For Remote Entry Level Leadership jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Remote Entry Level Leadership jobs in Chicago, IL look for?

The top searched job categories for Remote Entry Level Leadership jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Remote Entry Level Leadership jobs?

Cities near Chicago, IL with the most Remote Entry Level Leadership job openings:

Remote Entry Level Leadership jobs near you
Infographic showing various Remote Entry Level Leadership job openings in Chicago, IL as of August 2026, with employment types broken down into 75% Full Time, and 25% Part Time. Highlights an 44% In-person, and 56% Remote job distribution, with an average salary of $57,270 per year, or $27.5 per hour.

Now Hiring: Remote Jobs | Entry Level Leadership | Customer Service Rep. | Quick Hire | Start ASAP

American Income Life AO

Chicago, IL • On-site, Remote

$16.50 - $22.50/hr

Full-time

Posted 5 days ago

Job description

Now Hiring: Remote Jobs | Entry Level Leadership | Flexible Hours | Quick Hire | Start ASAP
Position: Entry Level Leadership
Location: Work from Home
Start Date: ASAP
Employment Type: Full-Time / Part-Time (Flexible)
Responsibilities
Handle inbound and outbound communications (email, chat, or phone)
Clearly explain benefit plans and help clients choose the best options for their needs.
  • Perform data entry and administrative tasks
  • Collaborate with team members virtually
  • Maintain professionalism and confidentiality at all times

Requirements
  • Strong communication skills (written and verbal)
  • Reliable internet connection and computer/laptop
  • Ability to work independently and manage time effectively

No experience required - we provide full training and support.
Must be available to start immediately
Benefits
Script and Communication Training - Master the art of client engagement with confidence.
Free Qualified Leads - Focus on building connections, not searching for prospects.
Comprehensive Free Training - Learn everything you need to succeed, no experience required.
Single parents or individuals who need a flexible work-from-home setup are highly encouraged to apply.
Free Mentorship Program - Get guided by top producers and leaders in the industry.
Daily Live Coaching Sessions - Stay motivated and up to date with proven sales techniques.
Ready to Start?
If you're ready to take the next step and build a career that's both fulfilling and rewarding, apply today! Join a team that values your success, and let's create a bright future together.
Your future starts now-let's make it amazing!

Apply