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Remote Leadership Development Jobs in Chicago, IL

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Opportunities for career growth and leadership development * Supportive and collaborative team ... Comfortable working independently in a remote environment * Organized with good time management ...

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Opportunities for career growth and leadership development * Supportive and collaborative team ... Comfortable working independently in a remote environment * Organized with good time management ...

New

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Opportunities for career growth and leadership development * Supportive and collaborative team ... Comfortable working independently in a remote environment * Organized with good time management ...

New

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Leadership Development Programs * Incentive Trips for Top Performers * Medical and Life Insurance for you and your family * Supportive Team Environment Apply Today Build a rewarding remote career ...

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Leadership Development Programs * Incentive Trips for Top Performers * Medical and Life Insurance for you and your family * Supportive Team Environment Apply Today Build a rewarding remote career ...

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Leadership Development Programs * Incentive Trips for Top Performers * Medical and Life Insurance for you and your family * Supportive Team Environment Apply Today Build a rewarding remote career ...

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Our company focuses on remote career opportunities, leadership development, mentorship, and helping motivated individuals grow in a flexible work-from-home environment. Through ongoing training ...

Showing results 41-60

Remote Leadership Development information

See Chicago, IL salary details

$34K

$79.8K

$137K

How much do remote leadership development jobs pay per year?

As of Aug 7, 2026, the average yearly pay for remote leadership development in Chicago, IL is $79,773.00, according to ZipRecruiter salary data. Most workers in this role earn between $60,300.00 and $93,200.00 per year, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive in remote leadership development, and why are they important?

To thrive in Remote Leadership Development, you need expertise in leadership theory, organizational development, and adult learning principles, often supported by a background in HR, business, or psychology. Familiarity with virtual collaboration tools (like Zoom, Microsoft Teams), learning management systems, and certifications such as CPLP or SHRM-CP is highly valuable. Exceptional communication, empathy, cultural awareness, and the ability to motivate and engage remote teams are crucial soft skills. These qualifications enable you to effectively design, deliver, and evaluate leadership programs that drive measurable growth in distributed and diverse organizations.

What is remote leadership development?

A Remote Leadership Development job focuses on training and mentoring leaders in virtual or distributed work environments. Professionals in this role design and implement leadership programs, provide coaching, and help organizations cultivate strong remote leadership skills. They may work with individuals or teams to enhance communication, collaboration, and decision-making. This role is crucial for supporting company culture, engagement, and productivity in remote or hybrid workplaces.

What are some common challenges faced in remote leadership development, and how can they be overcome?

One of the main challenges in Remote Leadership Development is building trust and engagement with participants who are spread across different locations and time zones. To overcome this, professionals utilize interactive virtual tools, schedule sessions to accommodate various time zones, and incorporate diverse learning methods to maintain participant interest. Another challenge is measuring the effectiveness of leadership programs remotely; this can be addressed through regular feedback surveys, virtual assessments, and performance tracking. Successful role-holders stay proactive by fostering open communication, encouraging peer learning, and continuously adapting their approach based on participant needs and organizational goals.

What are the most commonly searched types of Leadership Development jobs in Chicago, IL? The most popular types of Leadership Development jobs in Chicago, IL are:
What job categories do people searching Remote Leadership Development jobs in Chicago, IL look for? The top searched job categories for Remote Leadership Development jobs in Chicago, IL are:
What cities near Chicago, IL are hiring for Remote Leadership Development jobs? Cities near Chicago, IL with the most Remote Leadership Development job openings:
Infographic showing various Remote Leadership Development job openings in Chicago, IL as of August 2026, with employment types broken down into 1% As Needed, 81% Full Time, 15% Part Time, and 3% Contract. Highlights an 92% Physical, 2% Hybrid, and 6% Remote job distribution, with an average salary of $79,773 per year, or $38.4 per hour.

Entry Level Insurance Sales Representative (100% Remote)

Globe Life Insurance

Joliet, IL • Remote

$60K - $80K/yr

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

This job post has expired today. Applications are no longer accepted.


Globe Life Insurance rating

8.0

Company rating: 8.0 out of 10

Based on 22 frontline employees who took The Breakroom Quiz

164th of 303 rated insurance


Job description

Entry Level Insurance Sales Representative (100% Remote)

100% Remote | United States & Canada | Full-Time | Training Provided | No Cold Calling

Build a Career With Purpose, No Matter Where You're Starting

Your next opportunity doesn't have to look like your last one.

Whether you're a recent graduate searching for your first career, a veteran transitioning into civilian life, an experienced professional looking for a fresh start, someone exploring the financial services industry, or a licensed insurance agent ready for a supportive team, AO Globe Life welcomes individuals from all backgrounds.

We're looking for people who are motivated to learn, enjoy helping others, and want to build a career with long-term growth potential. Previous insurance experience isn't required, we provide the training and mentorship to help you develop the knowledge and confidence to succeed.

What You'll Do

As an Entry Level Insurance Sales Representative, you'll connect with individuals through scheduled virtual appointments to discuss insurance benefits they've requested information about. Your role is to educate clients, answer questions, recommend suitable coverage options, and guide them through the enrollment process when appropriate.

Every conversation is an opportunity to make insurance easier to understand while providing excellent customer service.

Responsibilities

  • Meet with clients through scheduled virtual appointments
  • Explain insurance products and benefit options in a clear, professional manner
  • Understand each client's needs and provide appropriate solutions
  • Assist eligible clients with the enrollment process
  • Maintain accurate records and follow up when needed
  • Participate in ongoing training, coaching, and professional development

What We Offer

  • 100% Remote Position (United States & Canada)
  • Qualified leads provided by the company
  • No cold calling
  • Comprehensive training and mentorship
  • Weekly commission-based compensation
  • Uncapped earning potential based on performance
  • Flexible work schedule
  • Opportunities for career growth and leadership development
  • Supportive and collaborative team environment

Who We're Looking For

We encourage applicants from a variety of backgrounds, including:

  • Recent graduates
  • Career changers
  • Military veterans
  • Professionals interested in the financial services industry
  • Licensed insurance agents seeking a new opportunity
  • Individuals with customer service, hospitality, retail, sales, or other people-focused experience

Successful candidates are:

  • Strong communicators
  • Willing to learn and accept coaching
  • Self-motivated and dependable
  • Comfortable working independently in a remote environment
  • Organized with good time management skills

Why Join AO Globe Life?

A meaningful career is about more than finding a job, it's about finding a place where your work matters and your growth is encouraged.

At AO Globe Life, you'll receive ongoing training, support from experienced leaders, and opportunities to continue developing your skills throughout your career. Whether you're building a new career from the ground up or bringing experience from another industry, you'll have the resources needed to grow professionally while helping individuals and families better understand their insurance options.

Apply Today

If you're looking for a remote opportunity where you can develop new skills, help clients make informed decisions, and build a career with growth potential, we'd love to hear from you.

Qualified applicants selected to move forward in the hiring process will be contacted by a member of our recruiting team. Please monitor your email, voicemail, and spam folder for updates.


What Globe Life Insurance employees say

Pay

Benefits

Hours and flexibility

Workplace

Get the full story on Breakroom


Globe Life logo

About Globe Life

Sourced by ZipRecruiter

Our Actions Today have a lasting impact on Tomorrow. Therefore, We aim to inspire everyone in our network to help Make Tomorrow Better. At Globe Life, We empower our Customers by offering products that help secure their Financial Future and Protect them from the unexpected. We give our Employees the chance to give back, Support Initiatives with a Service First Mindset, and Promote from within.

Industry

Insurance services and insurance agencies and brokerages

Company size

1,001 - 5,000 Employees

Headquarters location

McKinney, TX, US