The Possibility Well

Remote Leadership Strategist Opportunity | Executive Assistant Professionals

The Possibility Well
6 - 10 years
Chicago, IL
Part-time
Remote
1 month ago

About the role

Have you built a successful career as an Executive Assistant but find yourself wanting more flexibility, growth, and ownership over how you work moving forward?
We are seeking professionals from Executive Assistant and people-focused backgrounds who have built strong careers, bring valuable experience, and are now interested in exploring a model that offers greater flexibility, autonomy, and alignment with how they want to live and work.
This is an independent contractor role suited to professionals who are comfortable in decision-making, value continuous growth, and are proactive.
This opportunity may be a fit for professionals who:
Are looking for greater flexibility and ownership in how they work
Have strong communication and relationship-building skills
Enjoy supporting, guiding, and developing others
Are passionate about leadership, personal growth, and lifelong learning
Are open to exploring opportunities beyond traditional career paths
What You’ll Do:
  • Operate remotely with the autonomy to structure your schedule.
  • Engage in ongoing professional development focused on leadership, communication, mindset and digital strategy.
  • Facilitate structured, high-quality interviews with individuals exploring personal and professional growth opportunities.
  • Apply digital marketing systems and brand visibility strategies (training provided) to connect with a targeted, professional audience.
  • Collaborate with an international network of experienced, growth-oriented professionals.

What We Offer:
  • A fully remote, flexible work model designed around autonomy and ownership.
  • Access to established systems, training, and resources to support effective execution.
  • A professional environment that values experience, perspective, and ongoing development.
  • A performance-based compensation structure aligned with your results and contribution.

Ideal Candidates:
  • 5+ years of professional experience
  • Demonstrated strength in communication, relationship-building, and professional presence.
  • Ability to work independently with a high level of personal accountability.
  • Organized, self-directed, and comfortable managing priorities in a flexible structure.
  • Genuine interest in personal development and evolving how you work in your next chapter.

Note:
This is an independent contractor opportunity. It is not a salaried or employee position.
If you’re ready to apply your experience in a more flexible, growth-oriented, and future-focused environment, we’d love to connect.

Skills

Business Development and SalesProfessional Training and Coaching
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