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CEO-In-Training, Executive Director

Pennant

Milwaukee County, Wisconsin, United States · Full Time

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Experience
3–5 yrs
Salary
Openings
1
Posted
1 hour ago
Work mode
In office
Education
Bachelor’s degree
Resume
Required to apply

Job description

About the Role

Pinnacle, operating as part of The Pennant Group, is looking for entrepreneurial leaders with a strong track record of team leadership and a passion for senior living to join as a CEO-in-Training (CIT). This full-time salaried training program lasts between 3 to 6 months, tailored to the candidate's experience, preparing them to lead one of our assisted living, independent living, or memory care communities.

Training and Responsibilities

Participants will receive comprehensive hands-on learning in operations, clinical care, and business management, guided by an experienced Executive Director or CEO. The program includes mentorship, cross-departmental training, and active management responsibilities. Key activities include:

  • Immersive on-the-job training across operational, care, and administrative areas
  • Shadowing department leaders and frontline staff to grasp daily community routines
  • Leading live projects to improve host community operations
  • Studying applicable state regulations and senior living best practices
  • Developing leadership and interpersonal skills aligned with Pinnacle’s core values and mission

Qualifications

Minimum:

  • 3 to 5 years of leadership experience in any field
  • Demonstrable success in building and managing high-performing teams
  • Strong visionary and motivational skills with a focus on achieving results
  • Willingness to obtain required state licensure during the program
  • Flexibility to relocate as per opportunity availability

Preferred:

  • Bachelor’s degree; advanced degrees such as MBA or MHA advantageous
  • Experience in operations, financial oversight, or business growth
  • Entrepreneurial drive combined with a strong commitment to service

About Pinnacle Senior Living

As part of The Pennant Group, Pinnacle Senior Living operates with a mission to transform senior care through personalized service and empowered community leadership. We are supported by extensive clinical, legal, IT, HR, and accounting services, enabling our leaders to focus fully on exceptional resident care and team culture. Our core values include Customer Second, Accountability, Passion for Learning, Love One Another, Intelligent Risk Taking, Celebrate, and Ownership, creating environments where residents and employees flourish.

Work styles they’re looking for

Leadership Team Collaboration Team Leadership Passion for Learning

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