IT Systems & Security Compliance Specialist

IT Systems & Security Compliance Specialist

At WingXpand®

Locations:

Chicago (Schaumburg), IL

‍Type

Part-Time | Open 1/4/26 | Close 1/18/26

About WingXpand

WingXpand is Expanding What’s Possible™ with Autonomous Systems with our 8ft smart plane that expands from a backpack to help farmers grow more yield, public safety crews respond to disasters faster, and keep soldiers safe.

We’re a rapidly growing startup that is creating the future of smart, connected, robotics. We want you to play a key role in our journey!

Position Description

We are seeking a hands-on IT Systems & Compliance Specialist to support internal users, manage IT infrastructure, and help maintain compliance with CMMC Level 2, NIST 800-171, and related DoD cybersecurity requirements. This role combines help desk support, systems administration, network configuration, and security-focused IT operations in a Microsoft GCC-High environment.

Key Responsibilities

• Define requirements, source, install, configure, and maintain servers and core IT infrastructure.
• Administer systems in a Microsoft GCC-High environment, including identity, access controls, and secure collaboration tools.
• Support and maintain IT controls aligned with CMMC Level 2 and NIST 800-171 requirements.
• Install, configure, and support CAD and PDM software for engineering teams.
• Set up, configure, and troubleshoot networking equipment, firewalls, switches, and multi-site VPNs.
• Support secure remote access and segmented networks for government contract work.
• Assist with documentation, policies, and procedures related to cybersecurity, access control, and IT operations.
• Partner with leadership and engineering teams to support compliance audits, assessments, and continuous improvement efforts.
• Provide responsive help desk support for hardware, software, access, and connectivity issues.
• Work onsite out of the Chicago/Schaumburg office as needed to support secure systems and hardware.
  
  

Qualifications

• 5 years experience working as an IT Administrator, Systems Administrator, or similar role.
• Strong hands-on experience providing help desk and end-user support.
• Experience sourcing, installing, and configuring servers and networking infrastructure.
• Familiarity with CMMC Level 2, NIST 800-171, or similar cybersecurity compliance frameworks (hands-on or operational support).
• Experience working in or supporting a Microsoft GCC-High environment.
• Experience installing and supporting CAD/PDM software in an engineering environment.
• Working knowledge of VPNs, firewalls, network segmentation, and secure access controls.
• Ability to document IT systems, configurations, and compliance-related procedures clearly.
  
  

Additional Qualifications

• Experience writing a System Security Plan (SSP) for a regulated environment.
• Familiarity with POA&Ms, security control documentation, and audit readiness activities.
• Experience producing clear technical documentation, including system descriptions, security procedures, and operational guides.
  
  

What Else You Need To Know

To conform to U.S. Government aerospace technology export regulations, applicant must be a 'U.S. Person' (U.S. Citizen or a Permanent Resident/Green Card Holder).

We offer a competitive package based on level of experience, including the possibility of WingXpand stock options and advancement opportunities as the company expands.

If you are a self-motivated, results-driven individual with a passion for innovation and technology, we want to hear from you! Apply today and join us on the journey of expanding what’s possible with aerial intelligence for those that keep our world running!

Please apply with your resume and / or CV explaining why you are the perfect candidate for this role.