Senior IT Systems Administrator Automation & AI

The Opportunity

The IT team at UserTesting manages company-wide systems and serves as an integration, automation, and support point for the company's technology initiatives. The Senior IT Systems Administrator, AI & Automation manages critical platforms and helps set the technical direction for how they are configured, integrated, scaled, and secured across a large and varied enterprise tool set and a mixed macOS and Windows environment.

This role can lead platform initiatives end to end, from scoping and design through implementation and handover, and is accountable for the ongoing health, security posture, and lifecycle of the systems they own. Increasingly, that work includes connecting our systems to Automation & AI tooling enabling advanced capabilities in the platforms we already run, and building the integrations and access controls that let those capabilities operate safely.

Where an IT Systems Administrator can execute with approved designs, the Senior IT Systems Administrator produces the design, decides the approach with IT management, and reviews and validates changes requested for platforms they manage. The role is the senior technical escalation point for the IT team and mentors IT Systems Administrators and IT Support Specialists in the systems and practices behind that work.

Responsibilities

Platform Ownership, Automation, and Security

• Manage IT owned enterprise platforms including Okta, Google Workspace, and Intune  covering configuration standards, release management, integration patterns, and long-term roadmap.
• Lead platform initiatives end to end: requirements, design, sequencing, rollback and validation planning, and execution to completion.
• Own change management for assigned platforms, reviewing changes proposed by IT Systems Administrators and determining what requires escalation.
• Set and enforce technical standards across IT processes and applications, including automated provisioning models, group and permission strategy, SSO and SCIM patterns, vulnerability management, and automation and integration capability.
• Design and build integrations and automations using REST APIs, Okta Workflows, and scripting in Python and Bash; own the frameworks others build on, and keep the automation ecosystem current as applications and connected endpoints change.
• Stand up and maintain the integration layer that connects internal tools and data sources to AI systems, including MCP (Model Context Protocol) servers scoping access, managing credentials, and troubleshooting connectivity.
• Evaluate, enable, and govern AI features within platforms we already run (for example Atlassian Rovo, Claude, ChatGPT, Google Gemini), working with vendors and internal stakeholders on configuration, rollout, and usage guardrails..
• Assist the security and development teams in enforcement across assigned platforms, including least-privilege access design, configuration hardening, and vulnerability remediation; run periodic access reviews and produce evidence for internal and external audit.

Cross-Functional Delivery, Vendors, and Budget

• Partner with business system owners across departments to administer, integrate, and improve the tools their teams depend on, acting as technical advisor on selection and configuration.
• Improve cross-departmental processes spanning multiple systems, and maintain visibility of the application ecosystem including ownership, access patterns, integrations, and overlap.
• Improve manual processes across IT and other departments through automation.
• Assist in IT budget management through tool and license optimization, identifying underused spend, overlap, and consolidation opportunities.
• Research, evaluate, and run proof of concept work on new solutions including the fast-moving AI tooling ecosystem keeping the team's tooling current as the technology landscape changes.

Escalation, Enablement, and Documentation

• Act as the senior technical escalation point for the IT team, owning complex ITSM failures spanning multiple systems, leading root cause analysis, and driving the corrective actions that follow.
• Mentor IT Systems Administrators and IT Support Specialists, reviewing their configuration and automation work and deliberately transferring knowledge rather than retaining it.
• Author and maintain architecture documentation, access maps, runbooks, and administrative procedures including for integrations, automated workflows, and AI-connected systems and hold the team's documentation standard.

Requirements

• Able to work Monday through Friday in the US Eastern or Central time zone.
• 5+ years of experience administering enterprise IT systems in a system administrator capacity..
• Deep administrative expertise in enterprise identity (Okta, including Okta Workflows), Google Workspace administration, and endpoint management across a mixed macOS and Windows environment (Jamf, Intune)
• Proven ability to build integrations and automations using APIs and scripting languages like Python and/or Bash not only configuring vendor-provided features, but connecting tools together to improve functionality and output.
• Familiarity with API-based integrations: managing keys, scoping permissions, reading documentation, and troubleshooting connectivity between systems.
• Hands-on exposure to AI tooling in an enterprise context enabling and governing AI features in SaaS platforms, or standing up and securing AI integrations such as MCP servers. Certifications in AI platforms (AWS, Google Cloud, Anthropic) are a plus, but demonstrated hands-on experience is valued more highly; be prepared to walk through real examples.
• Track record leading technical projects affecting the entire company, including migrations or platform replacements, and stakeholder and IT project management.
• Experience producing audit evidence and operating access controls.
• Ability to work in a Kanban-style environment, managing due dates, incoming work, and technical debt effectively.
• Demonstrated ability to work directly with other departments on their tools and processes, translating business requirements into technical solutions.
• Willingness and ability to continually learn and grow. The technology space is constantly evolving, and we must evolve with it — this is especially true of AI, where change is unavoidable.

Don’t meet every single requirement but excited about the role? We encourage you to apply. Research shows that some candidates are less likely to apply unless they meet 100% of the qualifications—but you may be exactly who we’re looking for. Diverse perspectives drive innovation, and we’re committed to building a team with a wide range of backgrounds, experiences, and skills.

Application Process

• Meet with a Recruiter

• Meet the Hiring Manager

• Participate in a Panel Interview

• Final Interview (if applicable)

• Offer Stage

Accommodations

At UserTesting, we’re committed to creating inclusive and accessible experiences for all candidates. We believe diverse perspectives are essential to building exceptional products and experiences. If you require accommodations or would like us to tailor the interview process to better meet your needs, please contact us at [email protected].

UserTesting is an Equal Opportunity Employer and a participant in the U.S. Federal E-Verify program.  Women, minorities, individuals with disabilities and protected veterans are encouraged to apply.  We welcome people of different backgrounds, experiences, abilities and perspectives.  UserTesting will consider qualified applicants with criminal histories in a manner consistent with the San Francisco Fair Chance Ordinance, as applicable.