Systems Administrator II

About the role

Design streets that move people—not just cars. At Toole Design, we're leading the way in creating safer, more connected communities through sustainable multimodal transportation design. We're looking for a Systems Administrator II to join our IT team. We have a cloud-native identity and device management architecture aligning with Microsoft's modern best practices, so you'll focus on improving systems and efficiency, not patching legacy infrastructure.

Responsibilities

• Keep Toole Design's technology running smoothly across 24 office locations and remote teams, ensuring enterprise technology is dependable and teams productive.
• Design, maintain, and continuously improve infrastructure, ensuring secure, reliable systems that keep teams connected and productive.
• Provide Tier 2 helpdesk support; configure, maintain, and troubleshoot cloud services, hardware, and software.
• Take ownership of IT projects from planning through completion.
• Bring a collaborative, customer-first approach to directly helping staff solve problems.
• Mentor junior IT team members to help build a collaborative, continuously learning team.
• Influence technology decisions, lead meaningful initiatives, and continue to grow technical expertise alongside a collaborative IT team.

Requirements

• 5+ years of hands-on systems administration / IT experience, including Tier 2 support.
• Associate's degree or comparable technical training and experience.
• Strong written and verbal communication skills, with ability to build relationships and collaborate effectively across all levels of the organization.
• Experience implementing identity as part of a Zero Trust model (e.g., Conditional Access, PIM, SSO/SCIM, preferably Entra ID).
• Experience with endpoint management and application deployment (preferably Intune).
• Scripting and automation experience (PowerShell and Microsoft Graph preferred); familiarity using AI coding assistants to speed automation work is a plus.
• Working knowledge of networking, Wi‑Fi, and firewalls.
• Experience managing multiple projects to scope and schedule.
• Strong attention to detail and organizational skills.
• Ability and willingness to travel occasionally (3‑6 times per year) as needed to support business or project needs.

Benefits

• Collaborative, inclusive culture that supports growth and advancement.
• 8 paid holidays; at least 16 days of PTO accrual annually.
• Transportation perks.
• Opportunity to support projects that improve lives—advancing safe, inclusive design grounded in ethics, empathy, and equity.

Pay

Target salary range: $93,000 to $103,000.

Schedule

Flexible hybrid schedule: 3 days in the office and 2 days remotely.