Get the depth of qualitative interviews at the speed and scale of a survey with the power of AI-moderated research. Make better, faster decisions for your business. Backed by Y Combinator.
About the role
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.
What they're looking for
- 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
More about this role
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 Incumbents are outdated, slow, and burdened by high-cost services.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...
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