Director of Information Technology (IT)

WESTWARD360 ASSOCIATION MANAGEMENT LLC•Chicago, IL

4d•$130,000•Hybrid

About The Position

Westward360 is seeking a hands-on, strategic Director of Information Technology (IT) to lead the execution of our technology vision and roadmap. This role will oversee the full technology ecosystem — including proprietary systems, third-party platforms, integrations, cloud infrastructure, security, and end-user support. The ideal candidate is both a technical expert and operational leader who thrives in a fast-paced environment, can translate business needs into scalable solutions, and has a proven track record of managing complex platform changes. Westward360 is a rapidly growing national property management firm leveraging technology to deliver exceptional service, operational efficiency, and scalable growth. We manage a diverse portfolio of condominium, HOA, and rental properties across multiple markets. Our continued expansion requires forward-thinking leaders who can build infrastructure that supports both innovation and reliability.

Requirements

Bachelor's degree in Computer Science, Information Technology, or a related field.
5+ years of progressive leadership experience in a technology-focused role (Director, Senior Manager, or VP).
Expertise in Javascript/Google Apps Script development and enterprise integration via RESTful APIs (e.g., JSON).
Proven hands-on experience and knowledge of the Google Cloud and Google Workspace environment.
Demonstrated experience managing IT operations, including infrastructure, help desk, and vendor relationships.
Strong project management skills, specifically in leading major technology platform changes and migrations.
Excellent written and verbal communication skills in English, with the ability to communicate complex technical concepts to non-technical executive and operational teams.

Nice To Haves

A master's degree or equivalent experience is a plus.
Experience in the Property Management (PropTech) or real estate industry is a plus.

Responsibilities

System Integration & Architecture: Design, implement, and maintain the current and future architecture for all cloud-based software and API connections, ensuring reliable and scalable data flow across the organization.
Platform Migration & Implementation: Lead and project-manage major technology platform changes and new software implementations.
Security & Compliance: Oversee IT security protocols, data protection, and compliance across all technology systems.
Custom Code Management: Oversee the development, optimization, and maintenance of custom applications and scripts (primarily Google Apps Script/Javascript) used for bridging functional gaps between specialized software platforms.
API Management: Manage API access and data synchronization with core corporate systems, such as HR/Payroll (e.g., Paylocity), property management software (e.g., Vantaca), and communication tools (e.g., Zendesk).
Technical Roadmap: Translate business requirements from all divisions into a phased technical roadmap.
IT Infrastructure & Vendor Management: Manage relationships and service delivery from external IT partners for dedicated bandwidth, internet connectivity, and hardware lifecycle management.
End-User Support: Oversee the technical support function, ensuring timely and effective resolution for all software and hardware-related issues for US and offshore teams.25
Process Optimization: Continuously evaluate and improve technical workflows, troubleshooting challenging application integrations (e.g., Strongroom, Zendesk) to minimize business impact.
Team Leadership: Mentor, lead, and develop the internal and outsourced technology teams.
Project Governance: Drive projects to completion using modern project management methodologies, ensuring alignment with business goals and maintaining budget control.
Executive Partnership: Act as the primary liaison between the executive team, operations, and the technology department, clearly communicating risks, opportunities, and progress.