CEO-In-Training, Executive Director

Pennant; Indiana; On-site; USD 72,000 - 88,000; Full time

Job summary

Pinnacle Senior Living is seeking driven leaders for its CEO-in-Training (CIT) program, a salaried, full-time track designed to prepare you to lead a home health or hospice agency. The program lasts 3–6 months, with mentorship and cross‑functional training and hands-on operations experience.

On-site at Wisconsin locations, CITs may advance to Executive Director roles with continued mentorship, relocation opportunities as needed, and a pathway to future acquisitions within The Pennant Group

Qualifications

• 3-5 years of proven leadership experience.
• Strong track record of building and leading successful teams.
• Ability to create a vision and drive results.
• Must obtain any required state licensing during their CIT program (varies by state).
• Open to relocation based on available opportunities.

Responsibilities

• Participate in on-the-job training across all operational roles.
• Shadow clinical and administrative teams to understand the full scope of the business.
• Lead projects and contribute to real-time solutions within your host company.
• Engage in self-study on industry regulations and operational best practices.
• Align leadership skills while embodying Cornerstone’s core values.

Skills

Leadership experience

Team building

Strategic planning

Education

Bachelor's degree

MBA/MHA preferred

Job description

*This opportunity will require candidate to be on-site at one of our Wisconsin locations*.

Pinncle, part of The Pennant Group family, is currently seeking entrepreneurial leaders with proven results in building and leading exceptional teams—and a passion for the home health, hospice and home care industry. Join us in making an impact and shaping the future of post-acute care!

About the Opportunity:

The CEO-in-Training (CIT) Program is designed to prepare outstanding leaders for the opportunity to lead one of our home health or hospice agencies. This salaried, full-time training program typically lasts 3–6 months, depending on your background and experience. CITs may advance to oversee one of our thriving communities or a future acquisition, with continued mentorship and operational support from experienced Pennant partners.

As a CIT, you will gain hands‑on practical experience in operations, clinical care, and business management under the guidance of an experienced Executive Director/CEO. The program offers mentorship, cross‑functional training, and real responsibility in a dynamic environment. You’ll learn to drive results, cultivate a strong team culture, and develop a deep understanding of the unique business models that power Pennant’s success.

Key Responsibilities:

• Participate in on-the-job training across all operational roles
• Shadow clinical and administrative teams to understand the full scope of the business
• Lead projects and contribute to real-time solutions within your host company
• Engage in self-study on industry regulations and operational best practices
• Align leadership skills while embodying Cornerstone’s core values

Qualifications:

• 3-5 years of proven leadership experience
• Strong track record of building and leading successful teams
• Ability to create a vision and drive results
• Must obtain any required state licensing during their CIT program (varies by state)
• Open to relocation based on available opportunities

Preferred Qualifications:

• Bachelor's degree (MBA/MHA preferred)
• Entrepreneurial mindset with a passion for growth
• Experience in business development, marketing, and financial management
• Proven ability to drive culture and lead with passion

Compensation: $80K+ during the 12-18 week training period. Upon successful completion of CIT role and advancement to Executive Director role there is opportunity for base salary increase and incentive plan.

About Us:

Pinnacle Senior Living is part of The Pennant Group, a growing national organization with more than 250 affiliated locations across 17 states.

Our local leaders have significant responsibility for their communities and are supported by experienced operational partners and centralized teams in areas such as clinical services, accounting, legal, IT, and HR.

We believe in leaders who take ownership, hold themselves accountable, continue learning, and care about the people they lead and serve.

Our core values are:

• Customer Second
• Accountability
• Passion for Learning
• Love One Another
• Celebrate
• Ownership

If you are an experienced leader looking for an opportunity to learn a new industry and work toward leading your own senior living community, we encourage you to apply.