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Project Manager, Systems & Operations

CYM Living LLC

Chicago, Illinois, United States permanent

Posted: February 12, 2026

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Quick Summary

This Project Manager, Systems & Operations role in Chicago, IL is responsible for leading systems and operational projects from discovery through build, rollout, and adoption, with a focus on designing and building scalable workflows that improve execution across teams.

Job Description

This is a senior, hands-on role leading systems and operational projects from discovery through build, rollout, and adoption. The focus is on designing and building workflows, working directly in systems, and implementing practical solutions - not just managing timelines. The Project Manager will partner closely with field and corporate teams to understand current processes, identify gaps, and build scalable workflows that improve execution across teams.

While many initiatives will involve AppFolio, the role supports process and systems work more broadly and serves as an internal escalation point for system and workflow issues. This person will work directly with vendors, including AppFolio, to troubleshoot and implement solutions that support the field. We’re looking for someone who can operate independently, navigate ambiguity, bring structure to evolving processes, and drive projects forward in a complex operational environment.

Responsibilities

Project Ownership & Execution

• Lead systems and AppFolio projects from discovery through rollout
• Gather requirements and translate into clear workflows and solutions
• Manage timelines, priorities, stakeholders, and risks

Systems & Workflow Build

• Own the design, optimization, and ongoing performance of workflows across AppFolio and other operational systems
• Create SOPs, templates, and documentation

Internal Escalation & Vendor Coordination

• Serve as the internal escalation point for system and workflow issues
• Partner with vendors (including AppFolio) to resolve and implement solutions
• Coordinate testing and rollout of system changes

Training & Adoption

• Lead working sessions and trainings for new workflows
• Run live demos and hands-on sessions using real scenarios
• Clearly communicate expectations, ownership, and process changes
• Ensure teams know what to do and how to do it

Cross-Functional Collaboration

• Partner with Operations, Leasing, Maintenance, Accounting, HR, IT, and leadership
• Bring structure and practical solutions to complex operational challenges


Requirements:
• 5+ years of experience in project management, operations, or systems implementation
• Hands-on experience with AppFolio strongly preferred
• Experience building or improving workflows in operational systems
• Experience working with external software vendors
• Strong organizational, communication, and problem-solving skills
• Comfortable working in fast-moving, evolving environments
• Experience leading trainings or rollouts
• Property management or real estate experience preferred


Benefits:
• Competitive salary commensurate with experience
• Comprehensive health, dental, and vision insurance plans
• Retirement savings plan with employer match
• Paid time off and holidays
• Professional development opportunities and ongoing training

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