CEO In Training (CIT)

SupportFinity™; Wisconsin; On-site; USD 50,000 - 75,000; Full time

Job summary

SupportFinity™ is looking for candidates for its CEO-in-Training program in Wisconsin. This full-time position involves immersive training across operational, clinical, and business management aspects in senior living. Ideal candidates will have 3–5 years of leadership experience and the ability to inspire teams while achieving results.

As a CIT, you will shadow experienced leaders, engage in hands-on training, and learn to drive success in assisted living environments. This role may require state licensing during training, offers mentorship, and provides opportunities for future leadership positions.

Qualifications

• 3–5 years of leadership experience in any industry.
• Ability to inspire and deliver measurable results.
• Must obtain required state licensing during the CIT program.

Responsibilities

• Engage in training across operational and administrative functions.
• Shadow department heads to understand community life.
• Take the lead on real-time projects for community improvements.

Skills

Leadership experience

Building high-performing teams

Inspiration and vision setting

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

• 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

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.