As a Lead IT Support Engineer on Hillspire's IT Operations team, you will lead a team of IT Support Engineers on day-to-day IT support for our West Coast offices while remaining actively involved in resolving technical issues. You will support a diverse, high-touch environment serving more than 900 users across multiple affiliated organizations and locations. This role requires broad technical expertise across endpoint management, identity and access management, SaaS applications, basic networking, audiovisual systems, and enterprise AI tools. The successful candidate will also help identify and implement AI and automation solutions that improve IT support, employee self-service, documentation, and operational efficiency. Key Responsibilities • Provide technical guidance, mentoring, and daily work coordination for IT support team members. • Serve as an escalation point for complex, sensitive, or high-priority support issues. • Coordinate support coverage, ticket assignments, and workload across West Coast offices. • Establish and monitor service standards, SLAs, ticket quality, customer satisfaction, and operational performance. • Lead incident response and communications for significant service disruptions. • Promote consistent documentation, knowledge sharing, and adherence to established IT processes. • Participate in hiring, onboarding, training, and performance feedback for junior team members. • Provide professional, discreet, and responsive support to executives, principals, VIPs, and other high-touch users. • Administer and optimize Jira Service Management, Confluence, and IT asset-management workflows. • Manage endpoint lifecycle activities, including procurement, deployment, inventory, maintenance, replacement, and secure disposal. • Support conference rooms, audiovisual systems, executive meetings, and hybrid events. • Maintain accurate knowledge-base articles, technical documentation, runbooks, policies, and standard operating procedures. • Participate in vendor evaluations, product demonstrations, proof-of-concept testing, renewals, and implementation planning. • Provide occasional after-hours or emergency support for business-critical issues. • Travel occasionally to other offices or locations as business needs require. • Support and optimize various systems, including Google Workspace, Zoom, Slack, MDM, Okta, Microsoft Office, and other SaaS tools. • Identify opportunities to use AI and automation to improve help desk operations, employee self-service, onboarding, offboarding, documentation, and repetitive administrative processes. • Help develop, test, and maintain AI-powered support tools, including help desk agents, knowledge-base search, ticket summarization, categorization, and routing. • Support enterprise AI platforms such as ChatGPT Enterprise, Claude Enterprise, Gemini, and Atlassian Intelligence/Rovo. • Partner with IT, Information Security, Legal, and business stakeholders to evaluate AI tools for security, privacy, data protection, licensing, cost, and business value. • Create documentation and deliver training on the secure and responsible use of approved AI tools. • Monitor the performance and effectiveness of AI solutions and recommend improvements based on user feedback and measurable results. • Stay informed about emerging AI capabilities and assess their relevance to Hillspire's IT operations. Qualifications • Bachelor's degree in information technology, computer science, or a related discipline, or equivalent professional experience. • Seven or more years of progressive IT support experience, including experience in a senior, lead, or escalation role. • Demonstrated experience supporting executives and users in a high-touch, fast-paced environment. • Advanced experience administering Google Workspace and supporting macOS, Windows, iOS, and Android devices. • Hands-on experience with identity management, MDM, endpoint security, ITSM, and collaboration platforms such as Okta, Jira Service Management, Zoom, Slack, GAM, and Microsoft 365. • Experience administering or supporting enterprise generative AI platforms such as ChatGPT Enterprise, Claude Enterprise, Gemini, or Atlassian Rovo. • Demonstrated experience using AI, APIs, scripting, or workflow automation to improve IT operations or employee support. • Experience supervising, mentoring, or providing technical leadership to junior IT professionals. • Working knowledge of wired and wireless networking, TCP/IP, DNS, DHCP, VPNs, and basic network troubleshooting. • Strong written and verbal communication skills, sound judgment, discretion, and a service-oriented approach. • Ability to prioritize competing requests and remain calm when supporting urgent or sensitive issues. • Google certification and AI-related certifications are a plus. $140,000 - $150,000 a year This is an exempt position.