Mac IT Automation Engineer — AI-Driven Fleet Automation Lead

Adverb; San Francisco, Northern (CA, KY); Hybrid; USD 140,000 - 180,000; Full time

Job summary

Outset in San Francisco seeks an experienced IT Automation Engineer to lead our macOS fleet as a hands-on contributor. You will support employees directly while building secure systems, automations, and a long-term fleet strategy.

This role spans from diagnosing a single laptop to designing platform-wide solutions, combining Apple expertise, systems administration, automation, and high ownership. You will work onsite five days a week, with a focus on secure, scalable IT operations.

Qualifications

• Hands-on experience in client platform or endpoint engineering during rapid growth.
• Deep macOS administration skills including diagnostics, Apple hardware, networking.
• Mastery of Jamf Pro, Jamf Protect, Apple Business Manager, and modern enrollment practices.
• Current expertise in AI automation tooling and building AI-assisted workflows.
• Python and shell-scripting skills, plus API/webhook integrations with enterprise systems.
• Hands-on experience administering Rippling, Google Workspace, and Slack, with security focus.

Responsibilities

• Managing the macOS fleet lifecycle and long-term roadmap from architecture to secure retirement.
• Administering and improving Jamf Pro, Jamf Protect, Apple Business Manager, and related services.
• Providing responsive hands-on support for macOS hardware, OS, apps, identity, and network access.
• Building secure IT automations using AI tooling, Python, shell scripting, APIs, and webhooks.
• Partnering with teams to create secure automations for email/calendar, Slack apps, and integrations.
• Owning Slack security, apps, permissions, integrations, and workflows; coordinating with other platforms.
• Improving onboarding/offboarding, access management, device compliance, inventory, and support workflows.
• Creating documentation, runbooks, service standards, and technical plans.
• Collaborating with Security, Legal, People on access reviews and incident response affecting systems.

Skills

macOS administration

Jamf Pro

Jamf Protect

Apple Business Manager

Python

Shell scripting

APIs & webhooks

Slack administration

Google Workspace

Rippling administration

Tools

Rippling

Google Workspace

Slack

Jamf Pro

Jamf Protect

Apple Business Manager

Notion

Linear

Job description

Outset in San Francisco seeks an experienced IT Automation Engineer to lead our macOS fleet as a hands-on contributor. You will support employees directly while building secure systems, automations, and a long-term fleet strategy.

This role spans from diagnosing a single laptop to designing platform-wide solutions, combining Apple expertise, systems administration, automation, and high ownership. You will work onsite five days a week, with a focus on secure, scalable IT operations.