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Employee Support Specialist

MyPath · Brookfield, WI · Full time

Posted Sep 21, 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

Tell me about a time you helped raise morale for a group of employees. What did you actually do?

What they are checking: Whether they have concrete ways to support people beyond general encouragement.

Tell me about a time you built rapport with someone who was skeptical of you.

What they are checking: Whether they can earn trust with frontline staff who may see them as someone from the office.

What do you think makes direct care workers stay with an employer?

What they are checking: Whether they understand what drives retention in a demanding, often underpaid field.

What would you do

During a program visit you see a caregiver doing a task the wrong way. How do you give on-the-spot training without embarrassing them?

What they are checking: Whether they can correct practice respectfully and coordinate with the program supervisor.

A caregiver tells you they are thinking about quitting because of their schedule and stress. What do you do?

What they are checking: Whether they listen, find out what is fixable, and loop in the right people to keep good staff.

Staff ask you about a policy change you only partly understand. How do you respond?

What they are checking: Whether they admit what they do not know and get accurate answers rather than guessing.

This role requires a lot of driving between programs. How do you plan your week?

What they are checking: Whether they can organize travel and visits so every program gets attention.

About the work

You will run New Employee Orientation for direct care staff. How do you make a first day feel welcoming while covering required material?

What they are checking: Whether they see onboarding as the start of retention, not just a compliance checklist.

How would you use training guidelines to make sure every new hire gets the same experience, no matter who trains them?

What they are checking: Whether they value consistency, which keeps quality from depending on which trainer someone had.

How would you write a visit report about employee performance that is fair and useful to managers?

What they are checking: Whether they report facts and patterns clearly without turning reports into gossip or blame.

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The full job description

As published by MyPath.

Majority Women Employee-Owned. Empowered by Everyone to Transform Lives. Overview We are looking for an Employee Support Specialist (ESS) to join our team. The ESS supports and engages direct care employees through two core functions: Employee Onboarding and continued Employee Support and training. Through these responsibilities you will enhance the employee experience, drive employee satisfaction, increase performance, and build retention. Responsibilities Include: • Maintain program visibility and provide immediate training based on observations in coordination with program supervisor • Provide company updates, clarification of policy and procedures, and continued training to direct care staff • Facilitate New Employee Orientation training and education • Utilize training guidelines to ensure a standardized training experience • Engage with new and existing employees within programs to build rapport, promote job satisfaction, and promote morale • Generates reports recapping program visits and employee performance Benefits: • Full Benefits Package • 4 weeks of paid time off every year • $2000 Referral Bonus • Tuition reimbursement and Student Loan Pay-down programs • Employee Assistance Programs • And More! Qualifications: • High School Diploma or equivalent • Valid Wisconsin driver’s license for 3 years with an acceptable driving record • Maintain insurance on personal vehicle • 5 years caregiving experience, 1-2 years of supervisory experience preferred • Excellent communication skills • Ability to lead employee orientation and training sessions • Ability teach required skills and knowledge to direct care staff • Must be able to travel to different work locations, training sessions, and meetings Homes for Independent Living celebrates diversity and we are committed to creating an inclusive environment for all employees and clients. 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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