Systems Engineer I

Lessen

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Chicago, IL on site Until 10/5/2026 4+ years exp H-1B sponsor history First posted August 6, 2026 Last posted August 6, 2026
Job description
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. 

Compensation (from employer):
100000–115000 USD per year

About this role

Summary

Support and maintain server hardware, software, networking, and security systems.

Job title

Systems Engineer I

Experience level

4+ years

Minimum experience

4+ years exp

Industry

technology

Location requirements

Chicago, IL; remote not specified

Salary

$100k–$115k

Visa sponsorship

H-1B sponsor history

Management role

No

Skills & keywords

Required skills

Microsoft ServerCisco Unified CommunicationsVMWare or Hyper-VWindows Server 2008 R2 to 2016Exchange 2010 to 2016 or Office 365

Preferred skills

None specified

Specializations

server hardwareoperating systemsnetworkingsecurityvirtualization
Locations

Structured locations inferred from the posting.

Chicago, IL, USA

On-site City
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