---
title: 'IT Automation Engineer at Outset'
canonical: 'https://feeny.ai/job/it-automation-engineer-outset-san-francisco-51s41knafzqw'
type: 'job'
last_seen: '2026-10-19'
---

# IT Automation Engineer at Outset

- **Company:** Outset
- **Location:** San Francisco, CA
- **Compensation:** $145k–$195k
- **Employment:** full-time
- **Work type:** onsite
- **Posted:** 2026-09-23
- **Last confirmed live:** 2026-10-19
- **Apply:** https://jobs.ashbyhq.com/outset/13e23908-8de0-4cc3-90b1-a4746d3e2b65

## Job description

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 Incumbents are outdated, slow, and burdened by high-cost services.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.
- 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 and compliance 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.
- An exceptional customer-service mindset and empathy for employees blocked by technical issues.

Bonus

- 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.
- Experience in Detection & Response engineering, writing rules for EDR and SIEM, and automating remediation workflows
- Familiarity with zero-touch deployment, identity-driven access, device trust, and modern zero-trust architecture.
- Experience designing IT operations for a rapidly growing organization.

## About Outset

## Company Overview
- **One-liner**: Outset is an AI-moderated research platform that combines conversational AI, behavioral intelligence, and emotional analysis to let companies run high-quality qualitative interviews and research studies at massive scale.
- **Entity Type**: Private (Series B)
- **Headquarters**: San Francisco, California, United States
- **Founded**: 2022
- **Founders**: Aaron Cannon (CEO) and Michael Hess

## Core Business
- **Primary industry/industries**: Software Development / AI-Moderated Research & Insights Platform
- **Target customers**: Enterprise research teams (UX/Market/Consumer Insights), large corporations, and product teams (B2B, Enterprise)
- **Mission or purpose statement**: "The future of innovation begins with listening to humans." Understanding people’s needs, motivations, and behaviors is the hardest and most important challenge for businesses; Outset makes that understanding effortless and scalable.

## Products & Services
- **AI-Moderated Interviews**: Conduct hundreds of AI-moderated interviews simultaneously in any language (video, voice, or text). The AI moderator dynamically probes participants based on audio and visual cues to uncover the "why" behind answers.
- **Instant Synthesis & Analysis**: Automatically generates highly relevant summaries, themes, impactful quotes, and customizable highlight reels based on research objectives, eliminating manual tagging and sifting.
- **Participant Recruitment**: Recruit hundreds of participants directly within the platform, or share an interview link with any external list.
- **Guide Set Up**: Effortlessly set up interview guides using AI, with qualitative/quantitative questions, advanced probing guidelines, and intelligent skipping logic.
- **Easy Stakeholder Shareout**: Get instant top-line reports, custom AI-generated reports, highlight reels, and ready-to-share PowerPoint decks to integrate research into decision-making.

## Market Standing
- **Valuation/Market Cap**: Not publicly disclosed.
- **Key Metric**: Annual Revenue of USD 8,500,000 (as of latest data). Total Funding of USD 51,250,000.
- **Notable Investors/Partners**: Lead investors include **Radical Ventures** (Series B), **8VC** (Series A), with participation from 24 investors in earlier rounds. Trusted by enterprises like **Microsoft**, **Nestle**, **Uber**, **Hubspot**, and **Away**.
- **Growth Signals**: Massive headcount growth of **+563.6% year-over-year** (now 54 employees). Customer research coverage from 1.1B+ possible participants across 85+ countries, with over 500K studies run on the platform.

## Competitive Advantages
- Proprietary AI that bridges the "say-do gap" by probing in real-time based on audio and visual cues, not just recall.
- Multi-modal, multi-lingual scaling: enables research in any language, at any timezone, with continuous, multithreaded AI-moderated conversations.
- Enterprise-grade simplicity: designed for large research teams, removing scheduling friction and operations overhead so research happens in days, not months.
- End-to-end platform: from participant recruitment, guide setup, AI-moderation, to instant analysis and stakeholder shareout — a single integrated suite.

## Strategic Focus
- Expand leadership in replacing traditional, slow qualitative research (surveys, live interviews) with instant, scalable AI-moderated studies.
- Deepen enterprise penetration with top-tier clients (Microsoft, Nestle, Uber, HubSpot) by continuing to add advanced behavioral and emotional analysis features.
- Scale the platform’s capabilities to cover the entire research lifecycle more comprehensively, continuing to invest heavily in R&D.

## Why Work Here
- **Culture highlights**: "Supportive founders and seasoned investors foster community, without startup toxicity." Team is described as "smart, kind, and driven teammates who know how to make work fun." Founders are very hands-on and accessible.
- **Remote/hybrid/office policy**: Primarily in-office at a "million-dollar office space" in SF with sweeping views and quick access to Market Street.
- **Notable perks**: Daily catered lunches and snacks with flexible dietary options, unlimited PTO, comprehensive health insurance (medical/dental/vision), unlimited budget for productivity tools, commuter benefits, allowance for continuing education, 401k with 6% match.
- **Engineering culture**: A strong technical focus (backend and frontend engineers) working on state-of-the-art AI and NLP. 9 active job postings across sales, engineering, marketing, design, and operations.
- **Who should apply**: People passionate about AI, user research, and building products that make human understanding scalable. The company values balance, growth, and high-impact work without "startup toxicity."

## Sources
1. [outset.ai](https://outset.ai/)
2. [outset.ai/careers](https://outset.ai/careers)
3. [linkedin.com/company/outset-ai](https://www.linkedin.com/company/outset-ai)
4. [ycombinator.com/companies/outset](https://www.ycombinator.com/companies/outset)
5. [jobs.ashbyhq.com/outset](https://jobs.ashbyhq.com/outset)

## Other roles at Outset

- [Marketing Lead - EMEA](https://feeny.ai/job/marketing-lead-emea-outset-london-m76tbfccg8am) — London, United Kingdom
- [Platform Security Engineer](https://feeny.ai/job/platform-security-engineer-outset-san-francisco-t92pgz80ddez) — San Francisco, CA
- [Researcher](https://feeny.ai/job/researcher-outset-san-francisco-agq2gg9angkn) — San Francisco, CA
- [Head of Workplace Operations](https://feeny.ai/job/head-of-workplace-operations-outset-san-francisco-ss1by8ah9192) — San Francisco, CA
- [Account Director](https://feeny.ai/job/account-director-outset-san-francisco-yarryqq4qat7) — San Francisco, CA
- [Recruiting Coordinator](https://feeny.ai/job/recruiting-coordinator-outset-san-francisco-ty8cq9r4xk9w) — San Francisco, CA
- [Product Marketing Manager](https://feeny.ai/job/product-marketing-manager-outset-san-francisco-hv2qcx62mr95) — San Francisco, CA
- [Scaled Customer Success Manager](https://feeny.ai/job/scaled-customer-success-manager-outset-san-francisco-drq1c7t7mptp) — San Francisco, CA
- [Research Manager](https://feeny.ai/job/research-manager-outset-san-francisco-9gv2eapx6xyq) — San Francisco, CA
- [Program Manager - Research Operations](https://feeny.ai/job/program-manager-research-operations-outset-san-francisco-4h9qpq7d39j0) — San Francisco, CA