Senior IT Support Engineer

Knightscope•Sunnyvale, CA

10d•$115,000 - $135,000•Hybrid

About The Position

The Senior IT Support Engineer is the senior technical individual contributor on the Knightscope IT team and the escalation point of last resort before the Director of IT. The role owns Tier 2/3 engineering and escalation across a 250+ user Microsoft 365 and Okta-integrated environment, leads IT infrastructure and rollout projects end to end, and acts as the business analyst bridging department stakeholders and the IT stack. Beyond hands-on engineering, the position carries technical leadership responsibility — mentoring analysts, setting standards, owning runbooks and documentation, and driving service improvement across the ITSM function. The successful candidate is equally comfortable writing a PowerShell automation, running a project schedule with vendors and executives, and translating a business requirement into a system design. Knightscope’s IT team runs a modern, cloud-first stack supporting a hybrid workforce across engineering, operations, finance, and executive functions, plus an ongoing integration of the KSF subsidiary. This role sits at the center of that stack. You will own the technical depth behind endpoint, identity, and security operations while simultaneously carrying two or three concurrent infrastructure projects — security tooling rollouts, network and AV buildouts, ITSM automation, M&A-driven system integrations, and AI tooling deployment. You will work directly with the Director of IT on roadmap and budget, act as technical lead for the IT analyst team, and interface with Finance, HR, Security, Engineering, and outside vendors as the IT-side owner of business requirements. The environment is technically demanding, moves fast, and rewards people who take ownership, close loops without being chased, and document what they build. Candidates who thrive with autonomy, move decisively through ambiguity, and communicate clearly with both field technicians and executive staff will excel here.

Requirements

8–10 years of progressive IT experience in a corporate environment supporting Windows and macOS endpoints, including at least 3 years in a senior, lead, or escalation-tier role
Demonstrated project ownership — has independently run multi-month IT infrastructure or platform projects from requirements through cutover, including vendor and stakeholder management
Demonstrated business analysis capability — requirements gathering, process mapping, gap analysis, functional documentation, and vendor evaluation
Demonstrated technical leadership — mentoring junior analysts, setting technical standards, and reviewing the work of others; formal direct reports not required
Expert-level Okta SSO and Microsoft Entra ID administration — user lifecycle, MFA and conditional access policy, application SSO integration, SCIM provisioning, app assignment, and access provisioning/revocation; Okta Workflows automation experience required
Advanced hands-on experience with Microsoft Intune and Apple Business Manager — MDM enrollment, compliance policy, app deployment, and device lifecycle management at scale
Admin-level proficiency across Microsoft 365 — Exchange Online, SharePoint, OneDrive, Teams, and the M365 Admin Center; Exchange Online PowerShell required
Strong PowerShell scripting for task automation, bulk user and group management, and system administration, including scripting against Microsoft 365 and Okta APIs
Hands-on experience with Freshservice or a comparable ITSM platform at a configuration and workflow-design level, not just ticket handling — service catalog, automation rules, SLA policy, asset management, and reporting
Working knowledge of SentinelOne EDR and Microsoft Defender for Endpoint — agent deployment, policy management, and alert triage
Solid networking fundamentals — DNS, DHCP, VLAN segmentation, firewall policy, and switch-level troubleshooting in a managed environment (SonicWall, Aruba, or similar)
Practical fluency with AI tooling in a business context — Claude, ChatGPT, Replit, and AI-assisted ITSM automation such as Freshservice Freddi AI — including how to deploy, govern, and train others on it
Excellent written and verbal communication; able to write a clear requirements document, run a stakeholder meeting, and brief executives without hand-holding
Willing and able to work extended workdays and weekends as business needs require, including after-hours maintenance windows, cutovers, and incident response; must be available to work both on-site at Sunnyvale HQ and remotely, and to travel to other Knightscope and KSF sites as needed
Bachelor’s degree in Information Technology, Computer Science, or a related field preferred; an equivalent combination of education and hands-on experience will be considered

Nice To Haves

Experience supporting a publicly traded company, including SOX-adjacent IT controls and audit evidence production
Experience with M&A or subsidiary IT integration — domain, tenant, identity, and device consolidation
Slack Enterprise workspace administration, GitHub SSO integration, or Keeper Password Manager administration
Exposure to physical access control (Brivo) and AV/conferencing platforms (Neat, Logi, ClickShare)
Familiarity with business platforms adjacent to IT — NetSuite, ADP, HubSpot, Atlassian, or ClickUp
Conversational Spanish for supporting field and facilities teams
One or more of the following certifications: CompTIA Network+ or Security+; Microsoft MD-102, AZ-800, or SC-300; Okta Certified Administrator or Consultant; Apple Certified Support Professional (ACSP); ITIL Foundation v4; CAPM, PMP, or CBAP

Responsibilities

Serve as the Tier 2/3 escalation point for all hardware, software, connectivity, and identity issues across Windows and macOS endpoints; own root cause analysis and permanent fixes rather than repeat break-fix
Own the full device lifecycle — imaging and zero-touch provisioning, compliance policy, application packaging and deployment, patching, and secure decommission — via Microsoft Intune and Apple Business Manager
Design and maintain PowerShell automation for user lifecycle, bulk administration, license reconciliation, reporting, and Microsoft 365 / Okta API integrations
Administer the Microsoft 365 tenant at an advanced level — Exchange Online, SharePoint, OneDrive, Teams, security and compliance policy, and license optimization
Support and engineer conference room AV and event technology for company-wide meetings, earnings calls, and executive briefings
Maintain accurate asset inventory and coordinate hardware procurement and lifecycle refresh with vendors including CDW
Own Okta SSO and Microsoft Entra ID administration — application SSO integration, SCIM provisioning, group and app assignment rules, MFA and conditional access policy, and Okta Workflows automation
Administer endpoint security tooling (SentinelOne EDR, Microsoft Defender for Endpoint) including agent deployment, policy tuning, exclusion management, and alert triage; partner with Cybersecurity on incident response and remediation
Support network operations across HQ and remote sites — firewall policy (SonicWall), VLAN segmentation, DHCP/DNS, wireless, and switch-level troubleshooting
Enforce and document IT policy and access control standards; produce audit-ready evidence for internal and external review
Administer physical access control (Brivo), privileged remote support (BeyondTrust), and password management (Keeper) platforms
Own IT projects end to end — scope, requirements, budget input, vendor coordination, schedule, risk log, testing, cutover, and post-implementation support
Produce and maintain project artifacts: project plans, RACI, status reporting to leadership, change records, and closeout documentation
Coordinate cross-functional stakeholders and third-party vendors, holding them to committed dates and deliverables
Lead technical workstreams for subsidiary and acquisition IT integrations, including domain, email, identity, device, and application consolidation
Drive change management and end-user readiness for new platform rollouts, including training material, communications, and adoption tracking
Partner with department stakeholders to gather and document business requirements, then translate them into system requirements, workflow designs, and platform configurations
Map current-state processes, identify gaps and manual effort, and recommend automation or platform changes with a clear cost and effort case
Evaluate vendors and platforms — build comparison matrices, run proofs of concept, and produce written recommendations to support purchasing decisions
Own ITSM service design in Fresh service — service catalog, workflow automation, SLA policy, approval routing, asset records, and reporting
Build and maintain operational reporting on ticket volume, SLA attainment, license consumption, and asset position to support IT budget and headcount planning
Act as technical lead for IT Support Analysts — set standards, review work, provide direction on escalations, and develop skills through structured mentorship
Own the IT knowledge base and runbook library; enforce documentation discipline across the team
Serve as acting IT lead in the Director’s absence for operational decisions and escalations
Drive continuous improvement of support quality, response time, and first-contact resolution
Champion responsible adoption of AI tooling across IT operations and the broader business