Senior Support Engineer

ABOUT THE OPPORTUNITY

Workbox is seeking a full-time Senior Support Engineer to join our IT team. This is a high-impact, high-visibility role reporting directly to the Director of IT and working daily with teams across the organization to deliver reliable, secure, and user-focused IT services. The Senior Support Engineer will serve as the primary point of contact for employee-facing technology, providing L1 and L2 desktop support while ensuring endpoint reliability, security, and standards compliance. The Senior Support Engineer will also support and maintain meeting rooms and shared collaboration spaces, enabling seamless hybrid meetings for users joining from corporate and BYOD devices. This role is ideal for a hands-on technical professional who thrives in a fast-paced environment, enjoys being the frontline of IT support, and has deep experience supporting modern workplace technologies powered by Microsoft 365, Microsoft Intune, and meeting room technologies in a BYOD environment.

KEY RESPONSIBILITIES

• Serve as the primary escalation point for L1 and L2 desktop support, resolving end-user issues related to hardware, software, identity, and connectivity
• Provide hands-on and remote support for Windows, mobile devices, and peripherals in a BYOD and corporate device environment
• Manage endpoint lifecycle operations, including device provisioning, imaging, configuration, repairs, and decommissioning using Microsoft Intune / Autopilot
• Administer and support Microsoft 365 services including Entra ID (Azure AD), Exchange Online, Teams, OneDrive, and SharePoint
• Support and troubleshoot meeting room and collaboration technologies, including:
  • Room displays, cameras, microphones, speakers, and related systems
  • Presentation and video conferencing tools used by BYOD users
  • Ensure meeting rooms are consistently operational, user-friendly, and aligned with security and AV standards
  • Partner with hardware procurement and repair vendors to coordinate laptop and AV equipment setup, warranties, and break/fix services
  • Troubleshoot networking and access issues including Wi-Fi, VPN, DNS, DHCP, and basic VLAN-related problems impacting endpoints and meeting rooms
  • Monitor device and room technology health, proactively addressing performance or reliability issues
  • Support employees with Workbox-adjacent technology issues across coworking locations as part of field IT operations
  • Enforce security best practices such as device compliance, MFA, encryption, and access controls across endpoints and shared spaces
  • Document desktop, endpoint, and meeting room standards, support procedures, and troubleshooting guides
  • Participate in IT projects and initiatives related to modern workplace, endpoint security, collaboration tools, and user experience improvements

• 3?5+ years of experience in desktop support, IT field operations, or endpoint engineering
• Strong hands-on experience with Microsoft 365 administration and Microsoft Intune
• Experience supporting conference room and AV technologies in a BYOD or hybrid workplace
• Proficiency supporting Windows in a business environment
• Solid understanding of identity, endpoint security, and networking fundamentals (DNS, DHCP, VPN, Wi?Fi)
• Strong customer service mindset with clear communication and problem-solving skills
• Highly organized, collaborative, and comfortable supporting users in both office and field environments
• Willingness to be hands-on with end-user and AV issues while also contributing to long-term IT improvements
• Ability to work onsite in Chicago during standard business hours (8am-5pm, Monday-Friday), including occasional after-hours support as required.

• Experience supporting Microsoft Teams and BYOD solutions
• Familiarity with shared workspace or coworking environments
• Certifications such as CompTIA A+, Microsoft 365 Certified: Endpoint Administrator, or related IT certifications
• Experience working in fast-paced, high-growth environments
• Comfortable wearing multiple hats and owning outcomes from issue intake to resolution
• Passion for improving employee and guest technology experiences

Benefits Anticipated salary range: $75,000-$90,000 annually Comprehensive health benefits, including medical, dental and vision coverage Company-paid life insurance 401(k) plan Generous paid time off FSA, HSA and commuter benefits Ongoing training and professional development