Demo

Team Leader - Remote Career Transition

Wholehearted Lifestyle
Chicago, IL Remote Other
POSTED ON 5/2/2026
AVAILABLE BEFORE 5/30/2026
Ready for a Career Change with Autonomy, Flexibility and Purpose?

Are you an experienced Education, Leadership or Training Professional exploring a career transition into a more flexible, autonomous, and growth-focused role?

This is a unique opportunity to pivot your career into the thriving personal development space, where your existing skills in communication and coaching are highly transferable.

Step into a remote-first role that offers independence, and a clear pathway for growth - with full mentorship.

About The Organisation

We are a well-established, global organisation expanding our reach.

We are a people based business, specialising in leadership development and personal growth solutions.

Why This Role is Ideal for Career Changers

  • Bring Your transferrable skills
  • Leverage your teaching / training / coaching skills and experience in a new way
  • Transition into remote work / flexible location with flexible hours
  • Build skills in digital marketing, leadership, and business development
  • Follow a proven system with full training and mentorship
  • Create a scalable, performance-based income

Key Responsibilities

  • Engage in weekly interactive video-streamed training and leadership sessions
  • Learn and Implement digital marketing strategies to grow your client base
  • Conduct structured phone / video interviews
  • Manage your own schedule and productivity in a self-directed environment
  • Progress into leadership, training and mentoring responsibilities at your own pace

Ideal Candidate Profile

  • Background in education, corporate training, facilitation, or L&D
  • Seeking a career pivot, remote career, or lifestyle change
  • Strong communication and people skills
  • Self-motivated, organised, and goal-oriented
  • Open to learning online marketing and business development skills
  • Professional mindset with a desire for ongoing growth

What You’ll Gain

  • Fully remote role with flexible working hours
  • Structured onboarding and step-by-step training
  • Ongoing mentorship and leadership development
  • A proven business model with global reach
  • Performance-based, Scalable earning potential
  • Work-life balance aligned with your personal goals

Eligibility

  • Must be legally eligible to work in: Canada or USA
  • Minimum 4 years professional work experience required

Apply Now to Explore Your Career Transition

If you’re ready for a career change, to regain control of your schedule, and step into a role focused on growth, flexibility, and impact, we invite you to apply.

Submit your expression of interest today.

Shortlisted applicants will be contacted for an interview.

Hourly Wage Estimation for Team Leader - Remote Career Transition in Chicago, IL
$55.00 to $68.00
If your compensation planning software is too rigid to deploy winning incentive strategies, it’s time to find an adaptable solution. Compensation Planning
Enhance your organization's compensation strategy with salary data sets that HR and team managers can use to pay your staff right. Surveys & Data Sets

What is the career path for a Team Leader - Remote Career Transition?

Sign up to receive alerts about other jobs on the Team Leader - Remote Career Transition career path by checking the boxes next to the positions that interest you.
Income Estimation: 
$149,289 - $190,988
Income Estimation: 
$169,105 - $208,220
Income Estimation: 
$177,520 - $228,955
Income Estimation: 
$151,448 - $188,145
Income Estimation: 
$176,972 - $219,172
Income Estimation: 
$88,950 - $110,401
Income Estimation: 
$109,186 - $139,009
Income Estimation: 
$115,336 - $159,446
Employees: Get a Salary Increase
View Core, Job Family, and Industry Job Skills and Competency Data for more than 15,000 Job Titles Skills Library

Job openings at Wholehearted Lifestyle

  • Wholehearted Lifestyle Denver, CO
  • About The Role Are you a teacher, trainer, or education professional ready for a career pivot ? This is an opportunity for remote work to transition into a... more
  • 10 Days Ago

  • Wholehearted Lifestyle Boston, MA
  • Are You an Educator or Marketing Specialist Seeking Work-Life Balance? If you're passionate about growing, guiding, and facilitating growth, this remote ro... more
  • 10 Days Ago

  • Wholehearted Lifestyle Santa Rosa, CA
  • Are You an Educator or Marketing Specialist Seeking Work-Life Balance? If you're passionate about growing, guiding, and facilitating growth, this remote ro... more
  • 10 Days Ago

  • Wholehearted Lifestyle Los Angeles, CA
  • Are you currently working in education or marketing and starting to think about a change? If you're looking for a remote role with more flexibility , and y... more
  • 12 Days Ago


Not the job you're looking for? Here are some other Team Leader - Remote Career Transition jobs in the Chicago, IL area that may be a better fit.

  • Veregy, an Energy Transition Company Schaumburg, IL
  • Veregy is an award-winning NAESCO-Accredited decarbonization company focusing on accelerating and simplifying Energy Transition. We provide turnkey enginee... more
  • 14 Days Ago

  • Jenis Splendid Ice Creams LLC. Naperville, IL
  • In Oakbrook/Naperville, the starting hourly base pay rate for Team Jeni’s part-time Team Leaders is $16.00/hour with the opportunity to earn an average of ... more
  • 2 Days Ago

AI Assistant is available now!

Feel free to start your new journey!