MacOS IT Automation Engineer - AI-Driven Fleet Lead

Outset

San Francisco (CA)

On-site

USD 120,000 - 180,000

Full time

4 days ago

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Job summary

Outset is seeking an experienced IT Automation Engineer to lead our macOS fleet as a hands-on contributor. You will own the fleet lifecycle, from architecture to secure retirement, and build automation with AI tooling and scripting.

Based in San Francisco and onsite five days a week, you’ll administer Jamf Pro/Protect, Apple Business Manager, and related services, while enabling secure, scalable employee experiences and cross‑team automation initiatives.

Qualifications

Substantial hands‑on experience in client platform, corporate IT, or endpoint engineering, ideally during rapid growth.
Deep macOS administration expertise, including system logs, diagnostics, Apple hardware, peripherals, networking, and operating‑system subsystems.
Mastery of Jamf Pro, Jamf Protect, Apple Business Manager, and modern Apple enrollment and management practices.
Current expertise in AI automation tooling and experience building reliable AI‑assisted workflows, agents, or internal tools for enterprise systems.
Python and shell‑scripting skills, plus experience integrating identity, HR, collaboration, and device‑management platforms through APIs, webhooks, and event‑driven workflows.
Hands‑on experience administering and extending Rippling, Google Workspace, and Slack, including Slack security, applications, permissions, integrations, and workflow automation.
Experience diagnosing office network and Wi‑Fi problems safely in a live workplace.
Strong ownership and communication: you identify problems, develop sound solutions, explain tradeoffs, and follow work through to completion.
Sound judgment when working with privileged access, sensitive employee information, security incidents, AI systems, and internal investigations.

Responsibilities

Managing the macOS fleet lifecycle and long-term roadmap, from architecture, configuration, and deployment through procurement, maintenance, replacement, and secure retirement.
Administering and improving Jamf Pro, Jamf Protect, Apple Business Manager, and related Apple device-management services.
Providing responsive, hands‑on support for macOS hardware, operating systems, applications, identity, office networks, and Wi‑Fi, resolving issues during business hours with minimal disruption.
Building secure IT and security automations using current AI tooling, Python, shell scripting, APIs, webhooks, and lightweight integration services; establish standards for access, data handling, reliability, observability, and human oversight.
Helping other teams build secure automations for email and calendar workflows, Slack apps, internal support tools, and cross-system integrations.
Administering Slack—including security, applications, permissions, integrations, and workflows—and owning integrations across Rippling, Google Workspace, Jamf, and other internal platforms.
Improving onboarding, offboarding, access management, software deployment, device compliance, inventory, and support workflows.
Creating clear documentation, runbooks, service standards, and technical plans.
Partnering with Security, Legal, People, and business teams on access reviews, internal controls, incident response, and investigations affecting company systems.