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Outset is an AI-powered user research platform used by global brands like HubSpot, Microsoft, Uber, and Nestle to conduct qualitative research at scale. The company recently raised a $30M Series B and is experiencing rapid growth in the enterprise market.
You will lead Outset's macOS environment as a hands-on individual contributor, supporting employees directly while building secure systems, automations, and a long-term fleet strategy. This role combines deep Apple expertise, systems administration, automation, customer service, and high ownership. You will move fluidly from diagnosing individual laptop issues to designing platform solutions for the entire fleet. The role requires five days per week onsite presence, reflecting the company's office-first culture.
Key Responsibilities:
- Manage the macOS fleet lifecycle and long-term roadmap, including architecture, configuration, deployment, procurement, maintenance, replacement, and secure retirement
- Administer and improve Jamf Pro, Jamf Protect, Apple Business Manager, and related Apple device-management services
- Provide responsive, hands-on support for macOS hardware, operating systems, applications, identity, office networks, and Wi-Fi during business hours
- Build secure IT and security automations using AI tooling, Python, shell scripting, APIs, webhooks, and lightweight integration services; establish standards for access, data handling, reliability, observability, and human oversight
- Help other teams build secure automations for email and calendar workflows, Slack apps, internal support tools, and cross-system integrations
- Administer Slack, including security, applications, permissions, integrations, and workflows; own integrations across Rippling, Google Workspace, Jamf, and other internal platforms
- Improve onboarding, offboarding, access management, software deployment, device compliance, inventory, and support workflows
- Create clear documentation, runbooks, service standards, and technical plans
- Partner with Security, Legal, People, and business teams on access reviews, internal controls, incident response, and investigations
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: 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 qualifications include exceptional customer-service mindset, experience managing projects and knowledge in Linear and Notion, cybersecurity or corporate security background, familiarity with zero-touch deployment and zero-trust architecture, and experience designing IT operations for rapidly growing organizations.
