The IT Systems Technical Support Specialist I provides technical support to users by researching and answering questions and troubleshooting / resolving problems. They improve client references by writing and maintaining documentation and improve system performance by proactively identifying problems and recommending changes.
This is a part-time role up to 20 hours a week.
What You'll Do:
- Determine problem definition, research and resolution of Level 1 complexity and assists with Level 2.
- Coordinate problem-handling process for the information technology department
- Manage and update pending user’s requests using help-desk tracking system
- Escalate issues based on complexity and priority
- Perform administrative tasks involved with creation, deletion and changes in user’s network accounts
- Provide feedback to the team leader on key issues that affect IT services availability
- Advise users on system outages
- Be available for after-hours support/on-call when required
- Assist network/system engineers (when needed) with maintenance and troubleshooting by providing local on-site presence with direction from the engineers
- Install, configure and troubleshoot the following software products; Microsoft (MS) Office Suite, MS Windows 7/10, MS Active Directory, Email/O365, Anti-Virus products, Anti-SPAM products, and Remote Access methods (RDP, LogMeIn Rescue)
- Administer Microsoft Active Directory, Office365, S2 Security, and AWS Connect call-system
- Troubleshoot network and voice connectivity issues (with guidance from engineers)
- Troubleshoot printer and copier connectivity issues as well as monitor toner levels
- Configure and troubleshoot mobile devices, iPhone, Android
- Foster a positive team environment
- Ensure confidentiality of internal and external data
- Perform ad-hoc projects and other duties as assigned
What You'll Need:
- These are the professional skills we would expect from an individual fully established in this role.
- Customer Service - Advanced
- Verbal Communication - Proficient
- Written Communication - Proficient
- Teamwork - Proficient
- Relationships - Proficient
- Negotiation – Proficient
- Organizational Awareness – Proficient
- Learning Agility - Proficient
- Analysis - Proficient
- Problem Solving - Proficient
- Process Orientation - Proficient
- Prioritization - Proficient
- Computer Skills: Proficiencies in: Microsoft Word, Excel, PowerPoint, Outlook preferred
- Strong technical background on PC compatible type of hardware and peripherals
- Macintosh (Mac) support experience is a plus but not required
- Working knowledge of mobile devices; iPhone and Android
- Working knowledge of basic networking: Ethernet, TCP/IP, DHCP, and DNS
- System Experience with Microsoft products; Windows 7/10, Office 2013/2016, Active Directory, O365 preferred
- Undergraduate degree in Information Technology / Information System / Computer Science preferred.
- Able to work quickly and efficiently with a strong focus on achieving tasks.
- Proficient in soft skills and with a strong customer service focus
- 2+ years of experience in IT Technical Support field
Professional Skills
Role Specific Skills
Minimum Qualifications
Skills Required
- 2+ years of experience in IT Technical Support
- Customer service skills (advanced)
- Proficient verbal and written communication
- Proficient teamwork, problem solving and prioritization
- Able to work quickly and efficiently with strong task focus
- Proficiency with Microsoft Word, Excel, PowerPoint, Outlook
- Strong technical background on PC hardware and peripherals
- Macintosh (Mac) support experience
- Working knowledge of mobile devices (iPhone, Android)
- Working knowledge of basic networking: Ethernet, TCP/IP, DHCP, DNS
- Experience installing, configuring, and troubleshooting Windows, MS Office, Active Directory, Anti-Virus/Anti-SPAM, RDP, LogMeIn Rescue
- Administer Microsoft Active Directory, Office365, S2 Security, and AWS Connect
- Undergraduate degree in IT/Information Systems/Computer Science
- Availability for after-hours support/on-call as required
- Maintain confidentiality of internal and external data
What the Team is Saying
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Lessen LLC Compensation & Benefits Highlights
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Leave & Time Off Breadth — Flexible or 'unlimited' PTO and paid parental leave are highlighted, with volunteer time also appearing in the package. Feedback suggests time‑off options are a meaningful element, particularly for exempt roles.
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Healthcare Strength — Medical, dental, and vision coverage are paired with on‑demand counseling/EAP and wellness resources. Feedback suggests the core health offering is solid and broadly aligned with market norms.
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Wellbeing & Lifestyle Benefits — Perks include pre‑tax commuter options, pet insurance, and wellness programming, with some roles noting home‑office stipends. Feedback suggests these extras add breadth beyond the basics.
Lessen LLC Insights
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
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.
