IT Systems Administrator - Remote (Chicago Area)

ActiveProspect; Chicago (IL); On-site; USD 85,000 - 110,000; Full time

Job summary

ActiveProspect is seeking an IT Systems Administrator to join a small team responsible for our corporate network, including servers, workstations and laptops, connectivity, and end user support.

This role will help plan and execute upgrades, installations, monitoring, security practices, and capacity planning, while handling daily server monitoring and maintenance, backups, asset inventory, and support for our remote-first environment.

Qualifications

• 3 to 5 years of systems administration experience preferred.
• Bachelor's degree and/or relevant certifications are a plus
• Active Directory design and management skills
• Experience setting up Microsoft based systems, support mechanisms, and architectures
• Server support for Windows Server 2016 and above
• Desktop deployment and support for Windows 10/11 and macOS
• Experience with Hyper-V and IIS 10.x
• Experience with web farming and load balancing
• Experience with performance monitoring and server tuning for security and performance
• Experience with server auditing
• Solid network analysis and troubleshooting skills
• Familiarity with SQL Server 2019 and above
• Familiarity with network and endpoint monitoring software (VSA10, Iru, Endpoint Central)
• Familiarity with backup and recovery tools (Appassure/Quest)
• Familiarity with routers, firewalls, wireless access points, and managed switches
• File server maintenance, shares and quotas

Responsibilities

• Manage the corporate network, including servers and workstations
• Manage corporate Active Directory environments
• Manage server policies and login scripts
• Monitor servers for hardware and software performance issues
• Plan and coordinate upgrades, patches, and new corporate technologies
• Maintain an inventory of hardware and software assets
• Monitor daily and weekly backups
• Manage antivirus installations and scanning
• Manage Google Workspace
• Assist in management of our physical datacenters
• Assist with new employee onboarding and training
• Provide support as part of the Tier 1 technical support team
• Other duties as requested

Skills

Server administration

Active Directory

Windows Server

Networking troubleshooting

Documentation

Project planning

Communication

Customer service

Remote work support

Education

Bachelor's degree / certifications

Tools

Hyper-V

IIS 10.x

SQL Server 2019

Appassure/Quest

VSA10

Endpoint Central

Job description

Company Overview

ActiveProspect is on a mission to make consent-based marketing the best channel for online customer acquisition. We provide marketers the products they need to acquire qualified customers at scale. Our platform is trusted by thousands of companies engaged in direct-to-consumer marketing, helping them save wasted spend, comply with ever-changing regulations, and manage a constantly evolving partner landscape. Our flagship product, TrustedForm, is used to certify over 1 billion opt-in digital customer leads every year and is the gold standard for documenting prior express written consent for TCPA compliance.

Job Summary

ActiveProspect is seeking an IT Systems Administrator to join a small team responsible for our corporate network, including servers, workstations and laptops, connectivity, and end user support. This person will help plan and execute upgrades, installations, monitoring, security practices, and capacity planning, while handling the daily work of server monitoring and maintenance, backups, asset inventory, and support for our remote first environment. Success in this role comes from strong organizational habits, sound network management practices, and analytical thinking.

Responsibilities

• Manage the corporate network, including servers and workstations
• Manage corporate Active Directory environments
• Manage server policies and login scripts
• Monitor servers for hardware and software performance issues
• Plan and coordinate upgrades, patches, and new corporate technologies
• Maintain an inventory of hardware and software assets
• Monitor daily and weekly backups
• Manage antivirus installations and scanning
• Manage Google Workspace
• Assist in management of our physical datacenters
• Assist with new employee onboarding and training
• Provide support as part of the Tier 1 technical support team
• Other duties as requested

Qualifications and Skills

Technical

• 3 to 5 years of systems administration experience preferred
• Bachelor's degree and/or relevant certifications are a plus
• Active Directory design and management skills
• Experience setting up Microsoft based systems, support mechanisms, and architectures
• Server support skills for Windows Server 2016 and above
• Desktop deployment and support skills for Windows 10, 11 and macOS
• Experience with Hyper-V
• Experience with IIS 10.x
• Experience with web farming and load balancing
• Experience with performance monitoring and server tuning for security and performance
• Experience with server auditing
• Solid network analysis and troubleshooting skills
• Familiarity with SQL Server 2019 and above
• Familiarity with network and endpoint monitoring software (VSA10, Iru, Endpoint Central)
• Familiarity with backup and recovery tools (Appassure/Quest)
• Familiarity with routers, firewalls, wireless access points, and managed switches
• File server maintenance, including management of shares and quotas

Non-Technical

• Excellent project planning and delivery skills
• Solid written and verbal communication skills
• Ability to communicate task status, including progress and milestones
• Ability to prioritize tasks and manage overall workload
• Comfortable in a small, fast moving environment, and willing to step up and take ownership of deliverables
• Self-starter who can work with minimal supervision
• Keen attention to detail and quality of work
• Effective organization skills, with the ability to work on multiple projects at once
• Ability to communicate and interact with a diverse group of perspectives
• Strong customer service orientation
• Able to lift hardware up to 75 lbs
• Minimum 5-10% travel required

Reports to

• Senior Manager of IT

Direct Reports

• None

Organizational Impact

The IT Systems Administrator keeps the systems our teams rely on every day running reliably and securely. Because our business runs on the trust customers place in our platform and our handling of their data, the day to day discipline of this role, patching on schedule, verifying backups, tracking assets, and keeping access tightly controlled, directly protects both employee productivity and company risk posture.

• Supports every department by keeping workstations, network access, and collaboration tools available and performing well
• Reduces security and compliance risk through consistent patching, endpoint protection, access management, and server auditing
• Protects business continuity by monitoring backups so recovery is possible when something fails
• Shortens time to productivity for new hires by owning onboarding setup and training
• Works closely with IT leadership, department managers, and vendors, and serves as a visible front line for employee support
• Measurable indicators of success include ticket resolution time and volume, patch and backup completion rates, system uptime, asset inventory accuracy, and new hire setup turnaround
• Contributes tactically through daily monitoring and support, and strategically by helping plan upgrades, capacity, and the direction of our corporate architecture