Systems Engineer I

Posted Yesterday
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Chicago, IL, USA
Hybrid
100K-115K Annually
Mid level
Cloud • Real Estate • Software • PropTech
Help us revolutionize real estate services.
The Role
Administer, configure, and support server hardware, OS, messaging, SAN, backup and security systems. Troubleshoot complex server/network/voice issues, assist architecture and DR planning, support escalations and after-hours/on-site emergencies.
Summary Generated by Built In
Lessen is the tech-enabled, end-to-end property service provider that is transforming how commercial and residential real estate services are delivered and managed at scale. Lessen’s technology platform provides data-driven insights that unlock key growth opportunities for the entire real estate ecosystem—including investors, owners, managers, and service providers. The company leverages a network of over 30,000 vetted, qualified vendors (Lessen Affiliates) serving clients with over 1 million properties and completing more than 3.5 million work orders annually across an expanding range of services. Lessen, LLC is a venture-backed, privately held company with offices in Scottsdale and Chicago. 

Responsible for the configuration, implementation, and administration of the organization’s server hardware, operating systems, applications and integrations.  Analyzes and resolves complex problems associated with server hardware and server application software.  Detects, diagnoses, and reports problems on all hardware and software systems.  Performs a wide variety of complex tasks in software/hardware maintenance and operational support. Performs supervised liaison function between other Information Technology teams. Recognized as an emerging SME with comprehensive knowledge and experience and works under minimum to moderate supervision.  

What You'll Do:

    • Performs server configuration, implementation, maintenance and support in line with IT security and audit policies 

    • Responsible for the integrity, resilience and security of assigned systems 

    • Works closely with IT managers to plan, develop, design and strategize an architecture which will benefit the organization as a whole.  

    • Assist in developing the technology architecture of the firm, including but not limited to hardware, software, networking, systems and support processes and procedures. 

    • Helps superiors with trouble-shooting of system, network and voice hardware and software problems 

    • May assist in management and monitoring of Cisco Unified Communications Solutions; Voice Over IP, Call Manger, Voicemail, and Call Center 

    • Assists with assessing new technologies which may be appropriate to the mission of the company 

    • Helps and supports analysts with process and procedures within the IT department. 

    • Provides support for more technically complex issues and problems when escalated from Helpdesk 

    • Responsible for configuring, documenting, implementing and troubleshooting the following software products: Microsoft Server Operating Systems and Email Systems, Storage Area Network, Backup products, Anti-Virus products, and Anti-SPAM products 

    • Responsible for providing after hours support and on-site emergency response as needed 

    • Trouble-shooting server hardware operating systems and enterprise applications 

    • Administration and maintenance of server operating, messaging infrastructure and storage area network 

    • Directly works with superiors in the design and project management of network concepts, structure and connectivity, as directed 

    • Assists with daily backup of server data files, media, and offsite storage administration 

    • Fosters a positive team environment and assists superiors with the direction of team dynamics 

    • Ensures confidentiality of internal and external data 

    • Performs ad-hoc projects as needed 

    • Some travel as needed 

    • Other duties as assigned 

What You Need:

    • Bachelor’s degree in computer related field or equivalent experience  

    • Microsoft Certification or equivalent experience  

    • 4+ years of Information Technology experience supporting complex computer/system environments; or an equivalent combination of training and experience 

    • 3-5 years on a helpdesk 

    • 3-5 years’ experience with 

    • Ethernet network environment and peripherals 

    • Cisco Unified Communications Solutions; Voice Over IP 

    • HP, IBM or Dell servers 

    • VMWare or Hyper-V 

    • Windows Server 2008 R2 to Windows Server 2016 

    • Exchange 2010 to Exchange 2016 or Office 365 

    • providing customer service support network monitoring tools 

    • Experience with disaster recovery and planning concepts 

Why Lessen:
·        Competitive compensation
·        Health, Dental, Vision, Life, Disability options
·        401K retirement savings plan
·        Paid vacation, federal and floating holidays
·        Maternity/Paternity Pay
·        Career advancement opportunities
·        All the tools you'll need to be successful

Lessen is intentional about attracting, developing, and retaining amazing talent from diverse backgrounds. We’re looking for teammates that are enthusiastic, empathetic, curious, motivated, reliable, and will help us amplify the positive & inclusive culture we’ve been building.  Lessen is an Equal Opportunity Employer.  All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, protected veteran or disabled status, or genetic information. 

Skills Required

  • Bachelor's degree in computer related field or equivalent experience
  • Microsoft Certification or equivalent experience
  • 4+ years of Information Technology experience supporting complex computer/system environments
  • 3-5 years on a helpdesk
  • Experience with Ethernet network environments and peripherals
  • Experience with Cisco Unified Communications Solutions and Voice over IP
  • Experience with HP, IBM or Dell servers
  • Experience with VMware or Hyper-V virtualization platforms
  • Experience with Windows Server (2008 R2 through 2016)
  • Experience with Exchange 2010 through Exchange 2016 or Office 365
  • Experience with Storage Area Network (SAN) administration
  • Experience with backup products and offsite storage administration
  • Experience with Anti-Virus and Anti-SPAM products
  • Experience providing customer service support and using network monitoring tools
  • Experience with disaster recovery and planning concepts
  • Willingness to provide after-hours support and on-site emergency response

What the Team is Saying

Jay Payne
Kirby Pumper
Maya Shea
Jay McKee
Jennifer Gordon
Trevon

Lessen LLC Compensation & Benefits Highlights

  • Healthcare Strength Medical, dental, and vision coverage are paired with an employee assistance program offering on‑demand counseling, plus wellness programming/classes. Disability and life insurance are also included as part of the core package.
  • Leave & Time Off Breadth Flexible or “unlimited” PTO, paid parental leave, family medical leave, and volunteer time are part of the offering. These options point to broad time‑away support across categories.
  • Retirement Support A 401(k) with company match is available as part of the financial benefits. Pre‑tax savings options and related financial protections round out the package.

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The Company
HQ: Scottsdale, Arizona
713 Employees
Year Founded: 1999

What We Do

Lessen is the tech-enabled, end-to-end property service provider that is transforming how commercial and residential real estate services are delivered and managed at scale. Lessen’s technology platform provides data-driven insights that unlock key growth opportunities for the entire real estate ecosystem—including investors, owners, managers, and service providers. The company leverages a network of over 30,000 vetted, qualified vendors (Lessen Affiliates) serving clients with over 1 million properties and completing more than 3.5 million work orders annually across an expanding range of services. Lessen, LLC is a venture-backed, privately held company with offices in Scottsdale and Chicago. To learn more, visit Lessen.com.

Why Work With Us

We make caring for and improving properties simpler, faster, better. Powered by tech and perfected by people, we deliver best-in-class, transformational solutions to deliver assets to market faster, keep businesses up and running, and improve customer and resident experiences. We're property services, simplified.

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Lessen LLC Teams

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Residential
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Commercial
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Lessen Direct - A Mobile Technician Workforce
About our Teams

Lessen LLC Offices

Hybrid Workspace

Employees engage in a combination of remote and on-site work.

At Lessen, managers decide how teams work best—office, home, or hybrid. We value flexibility, connection, and outcomes, investing in tools that keep everyone aligned and focused on delivering great results together.

Typical time on-site: 3 days a week
HQScottsdale, AZ
Chicago, IL
Learn more

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