Technology Analyst

Clear Investment Group•Chicago, IL

2d•$75,000 - $90,000•Onsite

About The Position

This is an opportunity to configure, build, and improve the systems that keep a fast-growing real estate investment platform running — not just maintain them. You’ll implement changes, enhancements, and new configurations across our property management and financial systems. You’ll turn business needs and issues into tracked, completed work — owning your deliverables, status, and follow-through. You will be the connective tissue between CIG’s internal teams and our external AI consulting partner — keeping initiatives on track, ensuring nothing falls through the cracks, and helping the whole organization move in the same direction. This role will initially focus primarily on CIG's AI initiatives while building the business systems knowledge needed to support Yardi and related technology platforms. The goal is to develop hands-on familiarity with CIG's workflows, data, and ERP environment over the first several months, with the opportunity to take on broader Business Systems Analyst responsibilities as proficiency develops and business needs evolve.

Requirements

1–3 years of experience in a coordination, operations, project management, or technology implementation role
Hands-on familiarity with AI tools — you’ve incorporated them into how you work, you understand their practical applications, and you stay current on where the technology is headed
Experience with system support and data management
Moderate SQL and strong troubleshooting skills
Strong organization, communication, and follow-through
Exceptionally organized with strong attention to detail and the ability to manage multiple moving pieces without losing track
Natural communicator who can connect with people across all levels and functions — from a property accountant to a senior principal
Self-starter who takes ownership, follows through, and doesn’t wait to be told what to do next
Comfortable operating in a fast-moving, entrepreneurial environment where things change and priorities shift

Nice To Haves

Yardi, MRI, RealPage, or similar property management system experience preferred
Prior exposure to AI implementation, software rollouts, or technology change management
Experience supporting residential property operations preferred
Bachelor’s degree in Information Systems, Finance, or related field preferred

Responsibilities

Serve as the primary day-to-day internal point of contact for CIG's AI initiatives, coordinating closely with our external AI consulting partner and internal stakeholders.
Own the AI project tracker and keep workstreams, milestones, action items, decisions, and dependencies organized and moving forward.
Work across acquisitions, asset management, finance, accounting, operations, and other teams to understand workflows, gather requirements, identify practical AI use cases, and translate needs into clear deliverables.
Support the rollout of AI tools and workflows through testing, documentation, training coordination, internal communication, and follow-up to drive adoption.
Identify blockers early, coordinate resolution, and provide clear, concise status updates to leadership on progress, outcomes, open items, and next steps.
Use AI tools hands-on to support research, process improvement, testing, documentation, and automation, while helping evaluate what is working and where adjustments are needed.
Build a working knowledge of Yardi and its related property management and financial modules through structured learning, shadowing, and hands-on support alongside the Director of Technology and CIG's support resources.
Assist with business systems requests, issue tracking, configuration changes, enhancements, testing/UAT, reporting, dashboards, and user documentation as proficiency grows.
Support data validation and troubleshooting, including learning the underlying data structures and using SQL or other tools as needed to investigate and confirm results.
Assist with lease setups, migrations, conversions, and post-conversion reviews when applicable, while developing a practical understanding of how CIG's real estate, finance, and accounting workflows operate within Yardi.
Gradually assume greater ownership of Yardi and related systems work over approximately the first six months based on demonstrated proficiency, organizational priorities, and business need, with the potential to transition into a broader Business Systems Analyst role.
Turn requests, issues, and recommendations into clearly defined, tracked work items and maintain ownership of status and follow-through through completion.
Maintain organized documentation for project plans, system changes, vendor communications, testing, workflows, and user guidance so knowledge is retained internally.
Schedule and facilitate working sessions as needed, keep meetings focused on decisions and next steps, and ensure the right people have the right information at the right time.
Operate as a dependable liaison between business teams, technology resources, and external partners, with strong attention to detail, communication, and accountability.