IT Automation Engineer

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 Incumbents are outdated, slow, and burdened by high-cost services.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. 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. Bonus 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.