Systems Engineer

Lessen

On-site

Chicago, IL

Full-time

Entry

Mid Level

4+ yrs

Salary not listedPosted 1h ago

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Real job — pulled straight from Lessen’s careers page · Verified August 24, 2026 · No reposts.

Lessen is hiring a Systems Engineer — a full-time, based in Chicago, IL role. Apply directly on Lessen's careers page below.

Systems Engineer I

Team: Infrastructure Management

Location: Chicago, IL

Commitment: Full Time Employee

Workplace Type: onsite

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.