Assistant Operating Director - North Chicago, IL

Cornerstone Caregiving; Chicago (IL); On-site; USD 54,000 - 66,000; Full time

Benefits offered by this job

12 days PTO

Phone stipend

Career growth opportunities

Job summary

Cornerstone Caregiving in North Chicago, IL is seeking an Assistant Operating Director to lead in-office operations, oversee scheduling, and support staff. This role acts as second-in-command to the Operating Director to ensure high-quality client care and team performance.

Responsibilities include onboarding, coaching, and check-ins; managing recruitment and staff development; and maintaining process quality with state requirements. A fast-paced, people-first environment awaits you.

Qualifications

• Bachelor’s degree preferred but not required.
• 2+ years of management, leadership operations, or human resources.
• Experience hiring, recruiting, training, scheduling, and supervising staff.
• Leadership experience in healthcare or home care is a plus.
• Ability to work autonomously in a fast-paced environment.

Responsibilities

• Lead in-office operations and scheduling oversight.
• Coach and support in-office staff; align with Cornerstone standards and culture.
• Onboard and train new office managers; conduct weekly check-ins and reviews.
• Manage recruiting steps and staff oversight to support growth.
• Oversee client care scheduling, respond to escalations, and ensure quality.

Skills

Leadership

Operations management

Staff coaching

Scheduling

HR basics

Education

Bachelor’s degree preferred

Tools

Google Workspace

Job description

North Chicago, IL | Full-Time | Leadership Role |$60,000+ Benefits & Bonus Opportunities

AtCornerstone 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 than450offices, we are building strong in-office leadership teams to ensure every client and caregiver receives the highest level of care.

We are seeking anAssistant Operating Director (AOD), akey leadership roleand the Operating Director’ssecond-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 Operating Director’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.

Conductweekly 1:1 check-ins, performance reviews, coaching, and disciplinary action when needed.

Shareon-call rotationwith 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.

Conductcheck-up calls, quality visits, and client follow-ups to ensure satisfaction and care continuity.

Ensurestate-required supervisory visitsare completed (as applicable).

Serve as a backup for client assessments when the Operating Director is unavailable.

Qualifications

Bachelor’s Degreepreferred but not required, high school diploma or equivalent required.

2+ years of experiencein 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 workautonomouslyin 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, especiallyGoogle Workspace.

High attention to detail and exceptional follow-through skills.

Strong communication and interpersonal skills.

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 thecentral 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 adirect impacton 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.

**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.**

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