WinnCompanies
IT Support Specialist (Boston HQ: On-Site)
The Role
WinnCompanies is looking for an on-site IT Support Specialist to join our Boston Corporate Office. You will play a crucial role in ensuring the smooth operation of IT systems and services. Reporting directly to the Manager of IT Support Services, you will be responsible for on-going support of companywide networks, systems, and IT assets.
This role requires a solid understanding of Network/Systems administration, and the ability to troubleshoot and resolve technical issues. Additionally, this role requires experience supporting an end user community that is dependent on the computing/networking equipment provided to them.
This opportunity offers a salary range of $77,221.65 to $86,874.36, depending on experience. This is an on-site position with the following work schedule: Monday through Friday.
Responsibilities
- Diagnose, research, and resolve end-user issues in-person and remotely in a timely manner through established procedure and troubleshooting; escalate as necessary.
- Communicate and translate technical information to non-technical end users; maintain communication and monitor incidents through resolution.
- Act as an escalation point for requests not handled by first-level helpdesk support.
- Provide guidance and explain policies and procedures to end-users.
- Train end-users on new devices and technologies.
- Evaluate and address reported phishing emails; provide end-user guidance as necessary.
- Participate in the maintenance, implementation, and troubleshooting for software, hardware, and servers.
- Provide network connectivity monitoring and performance troubleshooting assistance.
- Assist in maintaining accurate hardware and software inventory.
- Review, update, and maintain documentation to ensure internal processes and procedures, workflows, and training aids are current.
- Assist with preventative maintenance within specified guidelines and procedures.
- Participate in review and evaluation of new hardware and software products.
- Support and administration of identity management services including Active Directory, Entra ID, Okta SSO, Okta MFA.
- Provide audio/video support for Microsoft Teams Rooms technology.
- Assist in department reporting, data maintenance, systems updates, and other tasks as required.
- Collaborate with other IT team members and stakeholders to plan and execute IT projects and company business initiatives related to technology.
Requirements
- Minimum 3-5 years’ experience in IT troubleshooting support role.
- Proficient experience troubleshooting hardware, software, and network issues in-person and remotely.
- Proficient with Windows 10/11 and the latest Microsoft Office Suite.
- Proficient in common administrative tasks in Active Directory.
- Experience with basic and advanced administrative tasks in Microsoft 365.
- Working technical knowledge of current Internet protocols, including DHCP, DNS, LAN/WAN, HTTPS, SFTP.
- 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
- Associate's degree in related field or equivalent work experience.
- Certifications such as CompTIA Network+, MCAAA, CompTIA Security+, Coding, Cisco CCNA, or Microsoft Certified: Azure Administrator Associate.
- Experience with programming and development.
Our Benefits:
Permanent full-time US employees are eligible to participate in the following benefits:
- Generous time off policies (including 11 paid holidays (12 for MA employees); Generous Accrued Time Off increasing with years of service; Generous paid sick time; Annual day of service; Floating Holiday)
- 401(k) plan options with a company match
- Various Comprehensive Medical, Dental, & Vision plan options
- Flexible Spending Account, Dependent Care Flexible Spending Account, Health Savings Account options with HSA annual employer contribution
- Long Term Disability and voluntary Short Term Disability; Basic Term Life Insurance and AD&D; optional supplemental life insurance
- Health Expense Reimbursement program (including gym memberships, equipment, and subscriptions)
- Tuition Reimbursement program and continuous training and development opportunities
- Wellbeing program (group challenges, seminars, opportunities to earn points to reduce medical premiums), Employee Assistance Program, & Commuter and Parking Reimbursement options
- Employee Corporate Discount Programs (Verizon Wireless, Home Depot Pro, Staples, and more!)
- Flexible and/or Hybrid schedules are available for certain roles
- Employee Relief Program supporting employees with unexpected hardships that place undue financial stress on them and their families
- To learn more, visit winnbenefits.com
Why WinnCompanies?
A job you can be proud of: WinnCompanies is a nationally recognized leader in apartment community management and development. Our team members are committed to helping people in the communities we serve and making a positive difference in their lives.
A job that challenges you: Our employees are responsible for our growth and success, and we challenge our team members to always be their best in our fast-paced, dynamic and rewarding workplace.
A job you can learn from: We offer multi-faceted leadership and learning opportunities to support our team members’ career growth and professional development.
A team that cares: We value teamwork, innovation, diversity and mutual respect. Through our recognition and rewards programs, we’re committed to celebrating and uplifting our team members.
About Us:
WinnCompanies is a mission-driven, national business focused on building and operating top quality affordable housing communities for individuals and families of all incomes, including members of the U.S. Armed Forces and their families. Our people are the source of our success – 4,300+ team members working together to create the best possible living communities in 27 states, Washington, D.C., and Puerto Rico.
Whether your skills are in operations, maintenance, leasing, compliance, marketing, IT, HR, accounting or finance, there’s a role for you at WinnCompanies. Your passion for excellence can help us make a positive impact in the lives of real people every day.
If you are a California Resident, please see our Notice of Collection here.
Salary will vary based on job responsibilities and scope, geographic location, candidate’s relevant experience, and other factors.
Current Winn employees should apply through this internal link.
WinnCompanies Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about WinnCompanies and has not been reviewed or approved by WinnCompanies.
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Leave & Time Off Breadth — PTO/ATO, front‑loaded sick time, an observed holiday list that includes MLK Day and Juneteenth, and a paid Day of Service indicate broad time‑off coverage. These elements, alongside references to a generous accrued time‑off plan, contribute meaningful flexibility.
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Healthcare Strength — Multiple medical, dental, and vision plan options are offered, including an HSA‑eligible plan with company HSA funding. Company‑paid basic life insurance and long‑term disability further strengthen the health and protection package.
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Wellbeing & Lifestyle Benefits — Support resources such as an Employee Assistance Program, an employee relief fund, and PerkSpot discounts add lifestyle value. Extras like referral bonuses, travel assistance, and service anniversary awards round out the package.
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The Company
What We Do
At WinnCompanies, we turn housing into homes. As a leader in property development and management, we’re creating a challenging, fast-paced workplace where teamwork, innovation and mutual respect are both valued and rewarded. We believe the relationships we build with each other are just as important as the work we do. Explore your passion within one of our three business units – WinnDevelopment, WinnResidential and WinnMilitary. Operations, sales, compliance, maintenance, marketing, IT, HR, accounting and finance. No matter your expertise, your work will impact people who are more than just residents to us. They’re individuals, families and heroes. Founded in 1971, we are committed to enhancing the lives of our communities. We fund college scholarships for residents; host community service and volunteer activities and more. Come join our 3,800 team members in making a difference in your local community. With more than 600 sites in 23 states and D.C., there’s a place here for you to grow your career.
