System and Support Engineer

Overview:

We’re looking for two experienced Senior IT Support Technicians to join our expanding IT team and play a critical role in scaling support for a rapidly growing organization. You’ll be embedded at the HQ, working directly with executives, providing high-touch white-glove support, and helping lead key rollouts and infrastructure initiatives.

Responsibilities:

• Primary point of contact for executive support—handle high-priority tickets and day-to-day tech needs for 30 execs.
• Provide 2nd and 3rd level support for Windows 10, Mac OS, Office 365, and enterprise collaboration tools.
• Lead and support rollouts of new technologies and hardware across the org, including onboarding hundreds of new users.
• Troubleshoot and support conference room tech: Cisco, Crestron, A/V setups, video conferencing hardware.
• Implement and support infrastructure and security projects, such as modernizing video conferencing, flexible workspace tools, etc.
• Support enterprise platforms: Box, Okta, Microsoft Teams, Office 365, Zoom, and MS Teams Voice.
• Support executive communications and phones: MS Teams Phone, Cisco voice systems, and conference room integrations.
• Assist in managing software deployment and license tracking using standard deployment tools and inventory systems.

Required Skills & Experience:

• 5 years in IT support, with 2 years supporting executives.
• Strong experience with Windows 10, Office 365, and Mac OS.
• Experience with Crestron, Cisco conferencing, and troubleshooting A/V environments.
• Proven ability to work independently, take initiative, and drive tech projects.
• Familiarity with enterprise collaboration and identity management tools (Okta, Teams, Box, Zoom, etc.).
• Customer-service mindset with clear communication and attention to detail.

Nice-to-Haves:

• Experience in fast-growing or scaling organizations.
• Certifications: Microsoft, Apple, Cisco, or ITIL.
• Familiarity with Flex workspace and modern office tech implementations.

The right person will have ~5 years of experience doing the work, all in person and ready to start!

Local (Chicago area) applicants only, no third parties. To facilitate the process, email me directly at b p e n n e y @ s i e r r a i t s . c o m with “WHITE GLOVE) in the subject line. Thank you for reading!