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 Incumbents are outdated, slow, and burdened by high-cost services.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 support our macOS environment as a hands-on individual contributor. You will enable 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, and customer service.

At Outset, we value high agency, high accountability, high alignment, and impatience. In this role, you will proactively pursue opportunities to improve our IT environment, own outcomes and fix issues when systems fall short, collaborate so the whole team wins, and move with urgency through clear communication and fast iteration.

Employees work in the office five days per week, so this hands-on role is also onsite five days per week. Our managed 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.