Senior IT Support Engineer

What you'll do

Onsite Support

• Serve as the primary onsite support lead for our San Francisco office, ensuring the reliability and performance of all local IT infrastructure.
• Lead or assist in the physical deployment and maintenance of hardware during planned projects and changes.
• Provide in-person, high-level support for issues and serve as the main on-site point of contact for IT within the San Francisco office.

Incident & Problem Management

• Maintain precise and up-to-date ticketing and project reports within IT systems.
• Act as the final escalation point for complex and recurring incidents that cannot be resolved by junior support engineers.
• Participate in an on-call rotation.
• Perform advanced troubleshooting and in-depth diagnostics to identify the root cause of systemic issues.
• Develop and implement permanent solutions or robust workarounds to restore service and prevent recurrence.
• Lead Root Cause Analysis (RCA) efforts for critical incidents, documenting findings and proposing long-term corrective actions.

Knowledge & Skill Development

• Create and maintain knowledge base articles detailing complex solutions, best practices, and troubleshooting guides to empower lower-tier support staff.
• Mentor and train junior support engineers to improve their technical skills and reduce the need for escalations.
• Participate in Major Incident Management teams, providing expert-level technical support to resolve high-priority outages quickly.

Proactive & Strategic Contributions

• Collaborate with engineering, development, and infrastructure teams to identify and resolve underlying service issues.
• Proactively monitor system performance and trends to identify potential problems before they impact users.
• Design, build, and scale AI-driven automations and agentic workflows to eliminate highly manual, repetitive internal tasks across departments.
• Integrate internal tools and ticketing systems (like Slack, Jira, or Google) with LLM APIs to build automated triage and response mechanisms.
• Provide technical input for new projects, system upgrades, and change management processes to ensure future services are reliable and supportable.
• Contribute to the continual service improvement of IT processes and services, aligning with ITIL principles.

What you bring

• 5+ years experience with Mac and PC technical support
• 5+ years experience working in a heavily SaaS-based environment (Google Workspace, Okta, Slack, Miro, Atlassian, Zoom, etc.)
• 4+ years coordinating with stakeholders to provide a high level of customer care with onsite support for executives and ICs within the Checkr office
• Ability to create strong connections with internal and external teams
• Deep understanding of computer fundamentals: networking, hardware & operating systems
• Experience performing hardware/software configuration and troubleshooting on MAC & Windows devices
• A positive attitude and excitement for building new processes and policies for a rapidly growing organization
• Ability to form strong relationships with internal and external stakeholders
• Experience with MDM (IRU, Intune)
• Ability to work daily in our San Francisco office.
• An A-player mindset with a strong bias for action: you raise the bar, move with urgency, stay resilient through ambiguity, and take ownership to deliver meaningful outcomes.

What We Offer

• A fast-paced and collaborative environment
• Learning and development allowance
• Competitive cash and equity compensation, and opportunity for advancement
• 100% medical, dental, and vision coverage
• Up to $25K reimbursement for fertility, adoption, and parental planning services
• Flexible PTO policy
• Monthly wellness stipend