Multifamily Technology Program Manager

29th Street•Chicago, IL

5d•$95,000 - $115,000•Remote

About The Position

From the West Coast to the East Coast and everywhere in between, 29th Street Property Management manages diverse multifamily properties. Ranging from high-end luxury assets to small-scale properties, 29th Street continues to grow. Our multi-billion-dollar collection of properties across the nation gives us an opportunity to continue to diversify our community portfolio, making us a multifamily industry leader. We offer a competitive benefits package of: 15 Paid Vacation Days, 6 Paid Sick Days, 11 Paid Holidays, Immediate Eligibility for Medical, Dental and Vision Insurance, Heath Savings Account, Short Term Disability, Basic Life Insurance, Pet Insurance, 401K and more! Come join our growing team! 29th Street is seeking a Multifamily Technology Program Manager to lead technology execution for property acquisitions, dispositions, third-party management onboarding, and portfolio-wide technology initiatives. You'll own the complete technology lifecycle for asset transactions - from pre-acquisition due diligence and risk assessment through integration and eventual disposition - managing telecommunications infrastructure, network systems, hardware deployment, property management system migrations, and vendor coordination. Success requires understanding both real estate asset lifecycles and technology infrastructure integration. You'll build transformation roadmaps and playbooks that bring structure to ambiguity, create business-focused reports for deal teams and executives, drive measurable outcomes, and serve as a trusted technical advisor who translates complexity into business impact.

Requirements

Proven ability to operate as both strategic thinker and tactical executor - independently diagnosing problems, designing solutions, and personally executing critical work without established playbooks, oversight, or safety nets
5+ years of project management experience, with at least 2 years in technology implementations, integrations, or transformation initiatives
Multifamily real estate industry experience with deep understanding of property acquisitions, dispositions, asset lifecycle management, and the multifamily real estate landscape
Direct experience managing technology aspects of real estate transactions, property management transitions, or similar complex integration projects
Project Management Professional (PMP) certification or equivalent formal PM certification
Technical literacy in IT infrastructure, telecommunications, property management systems, and network architecture with ability to assess existing infrastructure, evaluate contracts and SLAs, identify gaps and risks, and guide vendor teams - without hands-on implementation
Demonstrated experience implementing and configuring project management platforms (Monday, Asana, Smartsheet, or similar) as a system administrator and power user, not just end user
Excellent communication and presentation skills with ability to translate technical details into business implications and serve as trusted advisor to executives
Track record of managing multiple concurrent projects with competing priorities, tight deadlines, and complex stakeholder environments
Hands-on approach with strong attention to detail, ownership mentality, and ability to build processes that bring structure to unstructured environments

Nice To Haves

Hands-on experience with property management systems (Yardi, RealPage, Entrata, or similar) including implementations and data migrations
Background in telecommunications infrastructure, carrier management, network architecture, or hardware lifecycle management with understanding of multi-site connectivity requirements
Experience with technology due diligence processes, M&A integration projects, or business transformation initiatives
Understanding of commercial lease requirements, telecommunications service agreements, and regulatory compliance in real estate
Change management experience or certification with track record of driving technology adoption
Familiarity with ITIL, Agile, or other process frameworks and methodologies
Experience working in matrix organizations, managing through influence without direct authority, or coordinating across distributed teams in transaction-heavy environments
Data-driven decision-making with advanced proficiency in analysis and creating executive-level presentations that tell a story through data

Responsibilities

Acquisition & Disposition Technology Management Lead technology due diligence for acquisitions, managing vendor teams conducting infrastructure assessments to identify technology risks, integration requirements, gaps, and cost implications for deal teams
Create comprehensive technology assessment reports and business recommendations with measurable ROI projections for executive leadership and transaction stakeholders
Manage end-to-end technology integration for acquired properties including telecommunications infrastructure, carrier transitions, network deployment, hardware lifecycle management, and property management system migrations
Develop and execute technology cutover planning and transformation roadmaps for acquisitions, dispositions, and third-party management client onboarding to minimize operational disruption
Technology Project & Infrastructure Management Lead portfolio-wide infrastructure upgrades, system migrations, property management system enhancements, network infrastructure projects, hardware refresh cycles, and technology implementations that drive operational efficiency
Manage telecommunications and carrier relationships including contract negotiation, service provisioning, SLA management, network infrastructure deployment, multi-site connectivity initiatives, and project budgets throughout the lifecycle
Process Development, Change Management & Project Governance Design, implement, and maintain project management workflows using enterprise PM platforms (Monday, Asana, Smartsheet, or similar) as a system administrator
Develop standardized processes, playbooks, transformation roadmaps, and operational frameworks that bring structure to complex technology challenges and enable consistent execution across transactions and initiatives
Manage risk throughout project lifecycles - document risk, develop mitigation plans, and provide path to resolution
Create business cases inclusive of cost-benefit analysis, ROI projections, and metric tracking for technology initiatives
Vendor & Stakeholder Management Evaluate, manage, and coordinate technology vendors including MSPs, telecommunications carriers, due diligence contractors, and project-specific resources to ensure service delivery and accountability
Serve as primary technology liaison between corporate IT, property operations, deal teams, executive leadership, and external partners, translating technical complexity into business impact
Navigate complex organizational structures and influence cross-functional stakeholders to align technology execution with business objectives and regulatory requirements