IT Generalist (Boston HQ)

At WinnCompanies, our work starts with people — the residents who call our communities home, the neighborhoods we help strengthen, and the 4,600+ team members across 30 states, Washington, D.C., and Puerto Rico who make it all possible. As an award-winning owner, developer, and manager of high-impact, mixed-income apartment communities, we are proud to be one of the nation’s leading managers of multifamily housing and one of the largest operators of affordable housing communities.

We bring together people who care about quality housing, meaningful service, and making a difference every day. Through our innovative resident services platform and commitment to exceptional communities, we offer career opportunities for individuals who want their work to create lasting impact.

Interested in learning more? Visit WinnCompanies to explore our benefits, mission, communities, and career opportunities.

About the opportunity

WinnCompanies is looking for an IT Generalist to join our Corporate Headquarters located in Boston, MA. You will serve as an advanced technical resource within a Microsoft 365 and Azure environment, resolving complex issues involving identity, endpoint management, and cloud infrastructure that fall outside the scope of routine support.  

This role also supports property lifecycle activities, including evaluating property technology environments ahead of transition, assisting with technology integration as communities come onboard, and supporting the secure decommissioning of technology and accounts as communities exit the portfolio. The IT Generalist combines hands-on systems administration, end-user support, and independent technical judgment to keep IT infrastructure reliable and property transitions running smoothly. 

This opportunity offers a salary range of $87,000.00-$105,000.00 annually, depending on experience. The selected candidate will adhere to the following hybrid schedule: Monday through Friday from 8:00AM to 5:00PM EST with the ability to be remote on Fridays. 

Responsibilities: 

• Serve as the escalation point for complex issues across the Microsoft 365 and Azure environment, exercising independent judgment to diagnose and resolve advanced technical issues. 
• Assist in the development and implementation of automation solutions (scripts, workflows, scheduled tasks) that reduce manual effort across IT support and operations. 
• Support the onboarding & offboarding of communities, including evaluation of current state of technology, integration of technology, and decommissioning of technology. 
• Triage and resolve end-user support tickets covering hardware, software, and network access issues. 
• Assist in the maintenance of end-user asset management, including desktops, laptops, mobile devices, and peripherals. 
• Document recurring issues and maintain knowledge base articles and standard operating procedures. 
• Provision, modify, and deprovision user accounts and access across Active Directory, Okta, and Microsoft 365. 
• Perform routine infrastructure support tasks, including printers, conference room technology, and workstation imaging. 
• Ensure compliance with data security and access control policies during day-to-day support activities. 
• Maintain accurate IT asset inventory and equipment tracking records. 

Requirements: 

• Associate’s degree in information technology or a related field 
• Advanced technical computer skills are required for technical support specific to functional area and related systems. 
• Ability to summarize and communicate moderately complex information in varied written formats to internal and external customers. 
• Strong customer service orientation.  
• Excellent verbal and written communication skills.  
• Ability to communicate ideas in both technical and user-friendly language.  
• Highly self-motivated and directed, with keen attention to detail.  
• Able to prioritize and execute tasks effectively.  

Preferred Qualifications: 

• Bachelor’s degree. 
• Ability to assist in mentoring and training of junior-level support personnel. 
• Strong process improvement skills. 
  

Benefits & Perks
Eligible full-time U.S. employees enjoy a competitive benefits package, including:

• Generous paid time off, paid holidays, sick time, a floating holiday, and a day of service
• Medical, dental, and vision coverage, plus HSA, FSA, and dependent care savings options
• 401(k) with company match and company-paid life, AD&D, and long-term disability insurance
• Tuition reimbursement, professional development opportunities, and career growth resources
• Wellness programs, employee assistance resources, commuter benefits, and employee discount programs
• Flexible work options for eligible positions

Learn more about our benefits at https://www.winnbenefits.com.

If you are a California Resident, please see our Notice of Collection here.

It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.

Salary will vary based on job responsibilities and scope, geographic location, candidate’s relevant experience, and other factors.

Internal candidates, please apply here: Internal Careers Hub