Assistant Operating Director - South Milwaukee, WI

South Milwaukee, WI | Full-Time | Leadership Role | $50,000 + Benefits & Bonus Opportunities

At  Cornerstone Caregiving , we are dedicated to helping older adults age in place with dignity, compassion, and exceptional support. As we continue rapid nationwide growth across more than 450   offices , we are building strong in-office leadership teams to ensure every client and caregiver receives the highest level of care.

We are seeking an  Assistant Operating Director (AOD) , a  key leadership role and the Operating Director’s  second-in-command . This position leads in-office operations, scheduling oversight, staff support and development, client care quality, and communication with Home Base. If you thrive in a fast-paced environment, love developing people, and bring strong organizational and operational excellence to your work, this role is for you.

Office Leadership & Operations

• Serve as the OD’s primary in-office partner, helping drive daily operations and maintain a strong, cohesive work environment.
• Lead, coach, and support in-office staff; reinforce Cornerstone’s standards, values, and culture.
• Onboard and train new office managers, ensuring clarity, confidence, and consistent performance.
• Conduct  weekly 1:1 check-ins , performance reviews, coaching, and disciplinary action when needed.
• Share  on-call rotation with office leadership.
• Oversee administrative workflow and follow-through, including payroll notes, shift verification, and operations updates.
• Maintain accurate documentation in alignment with Cornerstone policies and state requirements.
• Assist with recruiting, onboarding steps, and staff oversight to support office growth.

Client Care & Quality Assurance

• Oversee scheduling operations to ensure timely coverage and an excellent client experience.
• Respond to client escalations with urgency, professionalism, and empathy.
• Conduct  check-up calls , quality visits, and client follow-ups to ensure satisfaction and care continuity.
• Ensure  state-required supervisory visits are completed (as applicable).
• Serve as a backup for client assessments when the Operating Director is unavailable.

Qualifications

• Bachelor’s Degree  preferred but not required , high school diploma or equivalent required.
• 2+ years of experience in management, leadership operations, or human resources.
• Experience hiring, recruiting, training, scheduling, and supervising staff.
• Leadership experience within the healthcare or home care industry.
• Ability to work  autonomously in a fast-paced environment.
• Comfort managing multiple priorities and shifting needs throughout the day.

Other Requirements

• Valid driver’s license and auto insurance.
• High proficiency with technology, especially  Google Workspace .
• High attention to detail and exceptional follow-through skills.
• Strong communication and interpersonal skills.

Compensation & Benefits

• Growth Bonuses
• Medical, Dental, Vision benefits package.
• 12 days of PTO annually.
• Phone stipend.
• Leadership development, mentorship, and opportunities for career growth as Cornerstone expands nationwide.

Why You’ll Love This Role

• You are the  central in-office leader , ensuring clarity, rhythm, and daily operational success.
• You will directly shape staff performance, team culture, and client experience.
• You’ll grow in leadership through hands-on coaching, development, and operational oversight.
• Your work makes a  direct impact on seniors, caregivers, and families in your community.

Join a mission that matters.

If you’re an energetic, people-first leader who thrives on organization, communication, and problem-solving, we’d love to meet you. Apply today and help guide a team that provides meaningful care to those who once cared for us.

** We are an equal opportunity employer and prohibit discrimination/harassment without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws.**