Senior Infrastructure and Systems Engineer

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Department: Information Technology

Office: Home Office

Location: West Springfield, MA

Job Description

About the Opportunity:

Aspen Square Management, one of the nation’s largest privately held real estate investment and property management firms with over $2 Billion in assets, is seeking an experienced Senior Infrastructure and Systems Engineer. In this role, the Senior Infrastructure and Systems Engineer is responsible for the ongoing maintenance, troubleshooting, deployment, and tuning of all networks, virtualization stack, and cloud endpoints, as well as associated on-prem systems and infrastructure in cooperation with the Network & Cloud Engineer. 

This includes but is not limited to current and future project work, as well as participation in the after-hours, on-call rotation. It is expected that this role will accept technical escalations from the helpdesk, when necessary, as well as provide mentorship to junior technicians in areas of expertise. A firmly held belief in the value of documentation is required.  Preferred skills and areas of knowledge include but are not limited to: Cisco networking, VMWare-based virtualization, Windows Server administration, hybrid O365 & Azure Exchange / AD environments; Cisco networking; Meraki networking, O365

This role will work closely with executive leadership to implement strategic IT initiatives. The ideal candidate is passionate about technology and can work within a dynamic, fast-moving, entrepreneurial organization.  Exceptional opportunities for growth, great culture, and an attractive compensation package make this a phenomenal opportunity!

About the Company

Based in West Springfield, MA with a portfolio across the country, Aspen Square Management is one of the largest privately held real estate investment and property management firms in the US. Founded by entrepreneur, philanthropist and real estate guru Harold Grinspoon, Aspen combines the energy and creativity of a startup, the benefits of a 60-plus year track record of success, the scale and financial resources of a large organization, and the close-knit feel of a family business.

Known for its fast-paced, entrepreneurial, people-centric culture, Aspen Square invests primarily in value-add multifamily real estate investment opportunities. (In other words, we buy apartment communities, renovate, rebrand, and reposition them, and then either hold properties for the long-term or sell them under the right circumstances.) We are investors AND owner/operators. Our current portfolio consists of 14,000 apartments located in 15 states throughout the country valued at over $2 billion. We employ about 600 employees, with approximately 100 of those employees working in the Greater Springfield area. “Aspenites” often start their careers here and grow with us for decades.


  • Virtual environment (VMWare) administration and maintenance, inc. physical hosts, switching, and storage.
    • Application of critical patches as needed, or regular, non-critical patches per regular schedule
    • Week-end check for snapshots on VM’s that can be culled when on-call
  • Network appliance configuration, troubleshooting, deployment, and maintenance in legacy and current infrastructures, including:
    • Firewalls – Cisco (sunsetting), Meraki, including ASA (sunsetting)
    • Routers – Cisco (sunsetting), Meraki
    • Switches – Cisco (sunsetting), Meraki

•     Cloud environment management, troubleshooting, and administration, including:

  • Azure AD
    • O365 – email and application licensing
    • O365 – legal holds as requested
    • O365 – Teams management and administration
    • Kace helpdesk, imaging, and patching platform administration and maintenance
  • Datto cloud backup management, including:
  • Troubleshooting of backup failures that occur when on-call, either during after-hours periods or upon resolution of standard business hours if failures on non-critical
  • File restores as requested
  • Datto / Backupify for O365 backups and data restores
      • Windows / Linux Server administration
  • Supporting and maintaining legacy and supported infrastructure and systems
      • IIS / SSL / TLS certificate management
      • VM system updates
  • WSUS and Kace-based update approvals for Windows endpoints; applying Windows updates after-hours to servers, workstations, laptops per regular schedule (one month after release for regular updates, ASAP for critical security patches) based on on-call schedule
  • Linux VM updates quarterly, or more often in the case of critical security patches
      • Upkeep of Vulnerability Management platform (Nexpost / Rapid7 InsightVM), informing patching efforts and strategies for end-user and infrastructure endpoints.
      • Managing and resolving escalations from the helpdesk, either by providing technical guidance, troubleshooting assistance, or by taking ownership of issue resolution.
      • Assistance with ongoing application licensing management, renewals, and headcounts on an annual basis or as needed.
      • Assistance with helpdesk tickets in all-hands-on-deck scenarios, in the event of staffing shortfalls or exceptional circumstances or high levels of submissions.
      • Projects as assigned.
      • On-going contribution to, editing, and quality-assurance of IT documentation.
      • Regular review of and response to internal and external communications by email, instant message, or phone.


  • Bachelor’s Degree in Business Administration, Management Information Systems or related field required.
  • Exceptional leadership, time management and organizational skills with an attention to detail.
  • Excellent verbal and written communication skills.
  • Strong analytical and problem-solving skills.

Compensation & Benefits Package:

  • Love your work and the people you work with!
  • Competitive salary commensurate with experience
  • Comprehensive benefits program to include health, dental and vision insurance
  • Flexible Spending Program
  • 401K Retirement Plan with generous company match
  • Long-term disability insurance
  • Hybrid work schedule
  • Great work-life balance
  • Informal, collaborative work environment
  • New offices in a great locational with convenient off-street parking
  • Apartment and bulk buying discounts

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