CEO In Training (CIT)

Pennant; Wisconsin; On-site; USD 52,000 - 70,000; Full time

Job summary

Pinnacle Senior Living, a portfolio company of The Pennant Group, is seeking entrepreneurial leaders for its CEO-in-Training (CIT) program in Wisconsin. This salaried, full-time track lasts 3–6 months and prepares you to run an assisted living, independent living, or memory care community, with mentorship and operating oversight.

As a CIT you will gain hands-on experience across operations, clinical care, and business management under the guidance of an Executive Director/CEO.

Qualifications

• 3–5 years of leadership experience in any industry.
• Proven success in building and leading high-performing teams.
• Ability to inspire, set vision, and deliver measurable results.
• Must obtain any required state licensing during the CIT program (varies by state).
• Open to relocation based on available opportunities.

Responsibilities

• Engage in immersive, on‑the‑job training across operational, care, and administrative functions.
• Shadow department heads and front‑line staff to understand the day‑to‑day rhythm of community life.
• Take the lead on real‑time projects and contribute to meaningful improvements within your host community.
• Study relevant state regulations and best practices in senior living operations.
• Align leadership and interpersonal skills with Pinnacle’s core values and mission.

Skills

Leadership

Team-building

Strategic thinking

Relocation willingness

Education

Bachelor’s degree (MBA, MHA, or related field a plus)

Job description

Pinnacle, part of The Pennant Group family, is currently seeking entrepreneurial leaders with proven results in building and leading exceptional teams and has a passion for the senior living industry. Join us in making an impact and shaping the future of senior care!

About The Opportunity

The CEO-in-Training (CIT) Program is designed to prepare outstanding leaders for an opportunity to run one of our assisted living, independent living, or memory care communities. This salaried, full-time training program typically lasts 3–6 months, depending on your background and experience. CITs may advance to lead one of our thriving communities or future acquisition, with continued mentorship and operational support from experienced 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

• Engage in immersive, on‑the‑job training across operational, care, and administrative functions
• Shadow department heads and front‑line staff to understand the day‑to‑day rhythm of community life
• Take the lead on real‑time projects and contribute to meaningful improvements within your host community
• Study relevant state regulations and best practices in senior living operations
• Align leadership and interpersonal skills with Pinnacle’s core values and mission

Qualifications

Minimum Requirements:

• 3–5 years of leadership experience in any industry
• Proven success in building and leading high‑performing teams
• Ability to inspire, set vision, and deliver measurable 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, or related field a plus)
• Experience in operations, financial management or business development
• Entrepreneurial mindset and a heart for service

Location: Onsite in Wisconsin

About Us

Pinnacle Senior Living, a portfolio company of The Pennant Group (NASDAQ: PNTG), is redefining the senior living experience with a commitment to personalized care, vibrant communities, and empowered local leadership. As part of the Pennant family—a growing national network with over 250 affiliated locations across 17 states spanning home health, hospice, and senior living—we operate with the independence and flexibility that allow our local leaders to truly make a difference. Pennant Services provides robust clinical, legal, accounting, IT and HR support, enabling our teams to focus on delivering exceptional service and care.

We are guided by the core values that shape Pennant’s unique culture:

Core Values

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

These principles drive us to create communities where residents and employees alike can grow, thrive, and feel at home.

The employer for this position is stated in the job posting. The Pennant Group, Inc. is a holding company of independent operating subsidiaries that provide healthcare services through home health and hospice agencies and senior living communities located throughout the US. Each of these businesses is operated by a separate, independent operating subsidiary that has its own management, employees and assets. More information about The Pennant Group, Inc. is available at http://www.pennantgroup.com.