Senior Living CEO-in-Training | Remote Leadership Path

Deercreekseniorliving; Wisconsin; On-site; USD 55,000 - 75,000; Full time

Job summary

Pinnacle Senior Living, a portfolio company of The Pennant Group, invites ambitious leaders to join its CEO-in-Training (CIT) program in Wisconsin. This salaried, full-time pathway typically lasts 3–6 months and aims to prepare you to run an assisted living, independent living, or memory care community with mentorship and practical experience.

As a CIT, you will gain hands-on exposure to operations, clinical care, and business management, shadow leaders, lead real projects, study state

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.
• 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.

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 experience

Inspire vision

Deliver results

Education

Bachelor's degree

MBA / MHA a plus

Job description

Pinnacle Senior Living, a portfolio company of The Pennant Group, invites ambitious leaders to join its CEO-in-Training (CIT) program in Wisconsin. This salaried, full-time pathway typically lasts 3–6 months and aims to prepare you to run an assisted living, independent living, or memory care community with mentorship and practical experience.

As a CIT, you will gain hands-on exposure to operations, clinical care, and business management, shadow leaders, lead real projects, study state