Systems Trainer

Location: Chicago, IL - Hybrid

Reports to: Director of Property Technology

About the role:

Cross Street is looking for an enthusiastic and people-first Systems Trainer to help our teams confidently adopt and maximize the technology that powers our business. This role is responsible for creating engaging training experiences, developing learning resources, and ensuring every employee has the knowledge and support they need to effectively use our systems.

Working in our Technology Department and with business leaders, you'll translate complex technology into practical, easy-to-understand training that improves productivity, consistency, and the overall employee experience. Whether onboarding new team members, launching new software, or reinforcing best practices, you'll play a critical role in helping our people embrace technology with confidence and in providing a feedback loop to the stakeholders working to innovate our tech.

What you'll do:

• Design and deliver engaging instructor-led and virtual training sessions for employees across the organization.
• Develop training materials including guides, videos, knowledge articles, and self-paced learning modules.
• Lead technology onboarding for new hires, ensuring they are equipped to use our systems from day one.
• Partner with department leaders and the help desk to identify knowledge gaps and create targeted learning plans.
• Support company-wide technology rollouts by creating adoption strategies, communications, and training programs.
• Maintain and continuously improve our technology knowledge base and training library.
• Measure training effectiveness through feedback, assessments, and system adoption metrics.
• Serve as a trusted resource for employees by answering questions and reinforcing best practices.
• Stay current on new features and enhancements across our technology platforms to ensure training content remains relevant.
• Initial focus: train new hires, Shared Services team members, accounting staff, and any employee needing a refresher on core Voyager 8 navigation, functions, and reporting, using an existing training agenda covering all applicable functions.

What we're looking for:

• Yardi Voyager 8 experience where you can train confidently on the platform from day one.
• You are passionate about helping people learn and succeed.
• You have experience delivering engaging training to audiences with varying levels of technical expertise.
• You can simplify complex concepts into clear, practical instruction.
• You are an exceptional communicator with strong presentation and facilitation skills.
• You are highly organized and able to manage multiple training initiatives simultaneously.
• You enjoy collaborating across departments and building relationships throughout an organization.

How you'll stand out:

• Experience training on CRM, ERP or other business technology platforms.
• Experience creating digital learning content, videos, and knowledge documentation.
• Familiarity with learning management systems (LMS) and adult learning principles.
• Strong proficiency with Google Workspace, Microsoft Office, and presentation tools.
• Experience supporting technology implementation or change management initiatives.
• Experience with real estate technology platforms is a plus.
• Experience with ZOHO is a plus.
• Bachelor's degree in Education, Training, Business, Technology, or a related field.