Director of Information Technology (IT) at WESTWARD360 ASSOCIATION MANAGEMENT LLC

Chicago, Illinois, United States -

Full Time

Start Date

Immediate

Expiry Date

27 May, 26

Salary

130000.0

Posted On

26 Feb, 26

Experience

5 year(s) or above

Remote Job

Yes

Telecommute

Yes

Sponsor Visa

Skills

Technology Vision, Technology Roadmap, Cloud Infrastructure, System Integration, API Management, Security Protocols, Platform Migration, Google Apps Script, Javascript, RESTful APIs, Google Cloud, Google Workspace, IT Operations, Vendor Management, Project Management, Team Leadership

Industry

Real Estate

Description

Description 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. What We Offer: Base salary up to $130,000 Monthly cell phone stipend Hybrid flexibility Medical/Dental/Vision insurance Front loaded PTO plus additional personal time 401k - Company match up to 4% Long and short term disability at no cost to employee Career advancement opportunity What You’ll Do: Technical Strategy & Architecture 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. Application Development & Customization 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 Operations & Support 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 & Project Leadership 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. What You’ll Need: Bachelor's degree in Computer Science, Information Technology, or a related field. A master's degree or equivalent experience is a plus. 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. Experience in the Property Management (PropTech) or real estate industry is a plus. About Westward360: Westward360 is dedicated to providing exceptional community management, rental management and brokerage services. Serving multiple markets throughout the United States, we have the systems, strategies, and expertise to meet the specialized needs of even the most demanding client. With more than 50,000 homes under management, we’re your all-in-one real estate solution. *Disability Notice: Disclosure is divulging or giving out personal information about a disability. It is important for the employee to provide information about the nature of the disability, the limitations involved, and how the disability affects the ability to learn and /or perform the job effectively. The employer has a right to know if a disability is involved when an employee asks for accommodations. Deciding if, when, and how to share disability-related information with a prospective or current employer can be overwhelming but we ask to please request a required accommodation prior to your first date of work. *Please note, a doctor's note may be requested by Human Resources, depending on the accommodation being requested, on a case-by-case basis.

Responsibilities

This role is responsible for leading the execution of the technology vision, overseeing the entire technology ecosystem including cloud infrastructure, security, and end-user support. Key duties involve designing system architecture, managing platform migrations, overseeing custom code development, and translating business needs into a phased technical roadmap.