IT Automation Engineer at Outset in San Francisco

Job description

• Application
• Outset invented a better way to do research: AI-powered user interviews.
• Global brands like Hubspot, Microsoft, Uber and Nestle use Outset to achieve deeper, qualitative insights about their users at unprecedented speed and scale.
• The research industry is massive (>$140B and growing) and ripe for disruption. Incumbents are outdated, slow, and burdened by high-cost services. That's our opportunity.
• Outset is backed by top Silicon Valley investors and raised a $30M Series B in December 2025—less than six months after our Series A—led by Radical Ventures with participation from M12 (Microsoft’s venture arm), 8VC, Y Combinator, and Adverb Ventures.
• The raise follows a breakout year, with our business growing 8x as enterprise customers across industries adopt our category, AI‑moderated research, as the new standard for understanding people.
• We’re a tight-knit team serving some of the world’s largest enterprises.
• We are looking for an experienced IT Automation Engineer to lead our macOS environment as a hands-on individual contributor. You will support employees directly while building secure systems, automations, and a long-term fleet strategy.
• This role moves fluidly from diagnosing a single employee’s laptop to designing the platform for the entire fleet. It combines deep Apple expertise, systems administration, automation, customer service, and high ownership.
• Employees work in the office five days per week, so this hands-on role is also onsite five days per week. Our employee computing environment is exclusively macOS; Windows support is not planned.

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.

Requirements

• 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.
• An exceptional customer-service mindset and empathy for employees experiencing technical problems.
• Experience managing projects, team knowledge, and a Help Desk system in Linear and Notion.
• Cybersecurity, corporate security, investigations, compliance, or legal operations experience, including incident response.
• Familiarity with zero-touch deployment, identity-driven access, device trust, and modern zero-trust architecture.
• Experience designing IT operations for a rapidly growing organization.

Skills

Required

• macOS administration
• Jamf Pro
• Jamf Protect
• Apple Business Manager
• AI automation tooling
• Python
• Shell scripting
• APIs
• Webhooks
• Rippling
• Google Workspace
• Slack

Preferred

• Customer service
• Project management
• Linear
• Notion
• Cybersecurity
• Incident response
• Zero-touch deployment
• Zero-trust architecture

Benefits

• $145K – $195K • Offers Equity