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Direct Support Supervisor/Lead Caregiver

MyPath · Sheboygan, WI · Full time

Posted Jul 14, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

This role requires working all three shifts and being on call. How does that fit your life?

What they are checking: Whether they can truly meet the availability requirement, which is non-negotiable for this role.

Tell me about a time you trained or mentored a new coworker.

What they are checking: Whether they can train, coach and mentor caregivers, which is the core of the supervisor role.

What would you do

A staff member tells you a coworker yelled at a client. What do you do?

What they are checking: Whether they report allegations of abuse to management right away instead of handling it quietly.

You get an on-call phone call at night that a client won't calm down. What do you do?

What they are checking: Whether they can guide staff by phone or come in when needed.

How do you keep guardians and case workers informed without overloading them?

What they are checking: Whether they communicate clearly and on time with outside parties, which the posting stresses.

How do you balance supervising staff with doing hands-on care yourself?

What they are checking: Whether they stay involved with clients while leading the team, which this hybrid role needs.

About the work

How would you manage a client's personal funds and keep a clear record?

What they are checking: Whether they handle client money with care and full accountability, since funds are easy to misuse.

How do you build a fair work schedule for the home?

What they are checking: Whether they can keep shifts covered while treating staff fairly.

Walk me through how you give medications and check that staff are doing it correctly.

What they are checking: Whether they know medication administration well enough to oversee others.

How would you plan meals for a client on a special diet?

What they are checking: Whether they follow dietary guidelines carefully, since mistakes can harm a client's health.

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The full job description

As published by MyPath.

Majority Women Employee-Owned. Empowered by Everyone to Transform Lives. Overview Training is provided, apply today! Must have a valid Driver's License! Must be able to work all 3 shifts and be on-call. HIL is looking for a Direct Support Supervisor (DSS) to join our team. A DSS will be responsible for supervising caregiver staff in the home, training, coaching and mentoring your team. Provide supervision of personnel and client care, enhancing the overall health, safety, and welfare of the clients and programming. As a Direct Support Supervisor , you will : • Maintain work schedules, training of staff, implementation of company policies and procedures • Management of client funds • Maintain excellent communication with guardians/case workers/management and overall health monitoring of clients • Report allegations of abuse, resident rights violations, conflict of interest, harassment, or fraud to management. • Maintain professionalism and confidentiality. • Interact with clients assisting with day to day tasks • Engage in fun activities with clients • Health monitoring and medication administration • Meal preparation in accordance to dietary guidelines • Light housekeeping • Assist with personal cares • On Call Responsibilities We offer: • Extra $1/hr. on 2nd shift AND Extra $2/hr. on weekends • Wage increases with experience • 3 weeks of PTO every year • Full benefit package, medical, dental vision, 401k, tuition assistance • And more! Benefits: • Competitive wages based on program and client needs • Referral Bonus Program - $2,000 Bonus per positive referral • Health, Dental, Vision, 401k, Life Insurance, Paid Time off, Company Stock • Access up to 50% of your earned money before pay day comes • Tuition Reimbursement and Loan Pay-down Programs Qualifications • Minimum of 18 years of age • Reliable transportation to and from programs and training classes • Communication & Problem-Solving skills • 1-2 years of previous supervisory experience preferred • Ability to work with individuals with special needs or willingness to learn • Managing stressful conditions by maintaining self-composure and self-control • Successful completion of a caregiver background check, TB test and Health Screen • Valid Driver’s License with 3 years of acceptable driving record, required Additional Information MyPath and its Operating Companies provide specialized services and dignified care for children, adolescents and adults with special needs. Our companies provide a spectrum of services and support which promote the ability of those we serve to live as independently as possible in the community. MyPath is composed of a beautifully diverse spectrum of employees with different characteristics, abilities, and life experiences. We believe that equitable, diverse, and inclusive practices in our workspaces are integral to the existence of MyPath. We value our diverse spectrum of Owners, the individuals we serve and the communities we encounter. Our success as an organization is directly proportional to our ability to create belonging and genuinely engage our Owners and potential Owners. We ask for demographic information so that we can be intentional in supporting our Owners best. Although not required, we would appreciate you sharing to help our commitment of cultivating a diverse, equitable, inclusive, and belonging MyPath. Our Culture At MyPath, we support an ownership culture throughout the organization. Our culture is based on our five beliefs and behaviors: • Passion • Accountability • Teamwork • Openness • Continuous Learning and Innovation As an employee owner, you can expect transparency, respect and appreciation. You’ll impact the place you work and map a career within MyPath. With your passion and our breadth of services, your options are nearly limitless! MyPath is proudly Majority Women Employee-Owned, with women leading at every level from the frontline to the boardroom. Our strength comes from all of us. Every Owner, regardless of gender, plays a vital role in shaping our culture, driving our mission, and building a workplace where opportunity and ownership are shared by all. MyPath is an Equal Opportunity Employer (EOE) committed to fostering a diverse, equitable, and inclusive workplace. We embrace the unique characteristics, abilities, and life experiences of our employees and believe that equitable and inclusive practices are essential to our success. We value the diversity of our Owners, the individuals we serve, and the communities we engage with.

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