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Senior Enterprise Strategist | Autonomous Advisory Path

True North Align


Job Location:

Chicago, IL - USA

Monthly Salary: $ 180000 - 180000
Experience Required: 5years
Posted: 4 September 2026 (2 days ago)
Application Deadline: 2 December 2026
Vacancies: 1 Vacancy

Job Summary

Many high-performing leaders reach a point where professional achievement no longer aligns with long-term fulfillment. Success shouldnt require trading personal autonomy for corporate security.

About the Organization:

True North Align collaborates with senior executives and established leaders through an autonomous advisory model designed for high-impact professionals. This role is designed for those ready to apply their expertise within a high-leverage organizational framework that prioritizes strategic flexibility leadership development and individual ownership over traditional institutional constraints.

Backgrounds We Value:

The capabilities required for success in this advisory role are developed in senior leadership positions. Professionals with proven track records as a Sales Executive HR Director Regional Sales Manager Strategic Advisor or HR Business Partner bring the strategic foresight necessary to leverage our executive leadership framework. Experience in Operations Management Corporate Training or Organizational Development is highly valuable for guiding candidate growth and strategic initiatives.

The Opportunity:

This path is tailored for accomplished leaders who have reached a plateau in traditional corporate structures. While the responsibilities are significant this role offers an alternative path to channel your leadership expertise into a growth-oriented independent practice.

Our Philosophy:

We believe continuous development is fundamental to sustained professional achievement. We provide a structured framework in the growing sector of Strategic Leadership and Executive Education built for leaders passionate about delivering measurable transformation.



Requirements

Professional Requirements:

  • 7 years of progressive professional experience with demonstrated leadership success

  • Proven ability to communicate with clarity authority and strategic vision

  • High level of personal accountability with a track record of driving autonomous outcomes

  • Strong capability in relationship-building and client engagement across executive levels

  • Commitment to continuous learning and professional development

Key Responsibilities:

  • Engage deeply with our proprietary leadership curriculum to deliver strategic guidance to clients

  • Drive results-oriented outcomes by facilitating executive development initiatives

  • Utilize modern communication tools and platforms to expand client reach and engagement

  • Collaborate with an international network of experienced leaders and strategy professionals

  • Cultivate and manage relationships with high-performing executives across major markets



Benefits

Role Advantages:

  • Fully remote structure with complete schedule flexibility

  • Direct alignment between executive impact and professional rewards

  • Access to a global executive network and comprehensive leadership resources

  • Autonomous work environment focused on strategic delivery rather than administrative oversight





Required Skills:

The Ideal Candidate: You communicate with clarity and authentic authority You take full responsibility for your outcomes and view challenges as opportunities 7 years professional experience with demonstrated success You value genuine connection and communicate with impact You thrive working autonomously and set your own standards for excellence Youre a perpetual learner always reaching for the next level


Required Education:

No degrees required