Senior IT Support Engineer

Knightscope•Sunnyvale, CA

9d•$115,000 - $135,000•Hybrid

About The Position

Knightscope (NASDAQ: KSCP) is seeking a Senior IT Support Engineer to join their IT team. This role serves as the senior technical individual contributor and the final escalation point before the Director of IT. The position is responsible for Tier 2/3 engineering and escalations within a Microsoft 365 and Okta-integrated environment supporting over 250 users. Key responsibilities include leading IT infrastructure and rollout projects from inception to completion, acting as a business analyst to bridge departmental stakeholders and the IT stack, and providing technical leadership by mentoring analysts, establishing standards, maintaining documentation, and driving service improvements within the ITSM function. The ideal candidate will be proficient in PowerShell automation, project management, and translating business needs into system designs. This is a full-time, exempt position, primarily on-site at Sunnyvale HQ, with flexibility for remote and after-hours work as required by business needs.

Requirements

8–10 years of progressive IT experience in a corporate environment supporting Windows and macOS endpoints.
At least 3 years in a senior, lead, or escalation-tier role.
Demonstrated project ownership — independently running 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, owning root cause analysis and permanent fixes.
Manage the full device lifecycle, including imaging, zero-touch provisioning, compliance policy, application packaging and deployment, patching, and secure decommissioning via Microsoft Intune and Apple Business Manager.
Design and maintain PowerShell automation for user lifecycle management, bulk administration, license reconciliation, reporting, and Microsoft 365 / Okta API integrations.
Administer the Microsoft 365 tenant at an advanced level, including Exchange Online, SharePoint, OneDrive, Teams, security and compliance policies, 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.
Own Okta SSO and Microsoft Entra ID administration, including 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, partnering with Cybersecurity on incident response.
Support network operations across HQ and remote sites, including firewall policy, VLAN segmentation, DHCP/DNS, wireless, and switch-level troubleshooting.
Enforce and document IT policy and access control standards, producing audit-ready evidence.
Administer physical access control (Brivo), privileged remote support (BeyondTrust), and password management (Keeper) platforms.
Own IT projects end to end, including scope, requirements, budget input, vendor coordination, schedule, risk management, testing, cutover, and post-implementation support.
Produce and maintain project artifacts such as project plans, RACI charts, status reports, change records, and closeout documentation.
Coordinate cross-functional stakeholders and third-party vendors, ensuring adherence to timelines 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 materials, communications, and adoption tracking.
Partner with department stakeholders to gather and document business requirements, translating 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-benefit analysis.
Evaluate vendors and platforms, building comparison matrices, running proofs of concept, and producing written recommendations.
Own ITSM service design in Freshservice, including 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, setting standards, reviewing work, providing direction on escalations, and developing skills through mentorship.
Own the IT knowledge base and runbook library, enforcing 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.