Training Development Jobs in Wisconsin (NOW HIRING)

Madison, WI | Primarily In-Person | Regular Day-Trip Travel to HMS Properties

At Horizon Management Services, we know that a strong start can make all the difference. We are looking for a passionate, organized, and people-focused Onboarding and Training Lead who is excited to help employees feel welcomed, supported, and prepared for success. This role will help create a consistent onboarding experience for property management employees while also supporting ongoing training, development, and continued growth across our HMS portfolio.

This is a great fit for someone who enjoys building relationships, bringing structure to busy environments, and helping others learn in a practical and encouraging way. You will work closely with HR, property leadership, managers, mentors, technology, compliance, and operations teams to make sure employees have the tools, guidance, and confidence they need to do their best work.

• Help welcome and support new hires, promoted employees, and team members transitioning into new HMS property roles.
• Create, maintain, and track onboarding schedules, checklists, training assignments, milestones, and follow-up items so employees and managers know what to expect.
• Facilitate training through one-on-one, small group, virtual, and onsite sessions that help employees understand HMS systems, workflows, policies, compliance expectations, and service standards.
• Support ongoing staff training and development after onboarding, including refresher training, skill-building sessions, process updates, and continued learning opportunities.
• Develop practical job aids, checklists, process guides, short training resources, knowledge checks, and other tools that make learning easier and more consistent.
• Use feedback, tracker data, recurring questions, and training trends to improve onboarding tools, training content, and follow-up processes.
• Support technology and systems training, including Microsoft 365, Paylocity, Grace Hill, OneSite, and other HMS-required platforms.

• You are organized, dependable, and able to manage multiple priorities while keeping details on track.
• You communicate clearly and kindly, and you can explain processes, expectations, and training content in a practical, approachable way.
• You enjoy helping others learn and are comfortable facilitating training, answering questions, and supporting employees with patience and professionalism.
• You can follow up respectfully and help hold others accountable while staying solutions-focused.
• You have experience coordinating onboarding, training, administrative programs, property management operations, HR processes, or employee support functions, or you are excited to grow in these areas.
• You enjoy creating helpful resources such as job aids, checklists, process documentation, training materials, or learning content.
• You bring curiosity, flexibility, and a willingness to learn about property management, resident service, compliance expectations, and operational workflows.

This is a meaningful opportunity for someone who wants to make a positive difference in the employee experience. In this role, you will help people feel more confident in their work, strengthen consistency across our properties, and support a culture of learning, teamwork, accountability, and continuous improvement. If you enjoy building structure, supporting people, improving processes, developing staff, and celebrating shared success, we would love to hear from you.

Successful candidates should be comfortable using Microsoft 365 tools such as Outlook, Teams, Word, Excel, SharePoint, OneDrive, Forms, Planner, and Lists. Experience with Paylocity, Grace Hill, OneSite, Trainual or similar learning platforms, video creation tools, or training content systems is a plus.

This position is based primarily at the Madison Corporate Office, with regular day-trip travel to HMS properties throughout the portfolio. Limited remote work may be approved based on tenure and business needs. Occasional adjusted hours may be needed based on training schedules, new hire needs, or property support requirements.