SECTION I · THE BRIEF
Brief #50582Updated 05 AUG 2026CHICAGO, ILLeverKHOSLA VENTURES
Employbl Company Profile

Systems Engineer I

Lessen is an online platform for managing properties and maintenance services.

Location
Chicago, IL
Company size
Posted
4w ago
Via
Lever
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Systems Engineer I · Lessen

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Job title
Systems Engineer I
Job location
Chicago, IL
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

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Where this role is based

Chicago, IL

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Lessen headquarters

Scottsdale, AZ

Founded

2019

Total raised

$735,000,000

View company profile ↗

Funding rounds

  • Series Unknown$500M
  • Series B$30M
  • Series B$170M
  • Series A$35M