ABOUT OUTMARKET Outmarket is the AI platform for insurance, trusted by more than 250 brokerages to run the work their business depends on. Commercial insurance still runs on dense documents and slow, manual workflows, and that is exactly what we automate: quote comparisons, coverage gap and tower analysis, policy review, and proposal generation, all grounded in our customers’ own data and source-cited so teams can trust the output. The impact is concrete. Teams save 12 to 15 hours per person every week, cut errors by roughly 65 percent, and win more business, all on infrastructure that is SOC 2 Type II certified, single-tenant, and never used to train AI models. We are an AI-first company in both what we build and how we work, shipping quickly and in close partnership with the agencies that rely on us. WHAT YOU’LL GET A high-impact role with ownership from day one. Competitive compensation and meaningful equity. Direct collaboration with founders and real users. Remote-first flexibility. The opportunity to help build an AI-native product from the ground up. ABOUT THE ROLE We are hiring an IT Engineer to own our internal systems and corporate IT: identity, devices, SaaS, and the automation that keeps the company running smoothly and securely as we scale. WHY THIS ROLE Own internal IT end to end and set how the company operates as it grows. Blend systems administration, security, and automation in one role. Directly improve every employee’s day-to-day experience. WHAT YOU’LL DO Own identity and SSO (e.g., Okta) and provisioning into downstream tools (Google Workspace, Slack). Manage device lifecycle and endpoint security (MDM), and harden internal systems. Administer SaaS applications, access, and licensing; run onboarding and offboarding. Automate internal IT workflows and provide responsive support to the team. Maintain internal networking and contribute to security and compliance posture. WHAT WE’RE LOOKING FOR 3+ years in IT engineering / systems administration / IT operations. Hands-on with identity/SSO (Okta or similar), Google Workspace, and MDM/endpoint tooling. Scripting/automation ability (e.g., Python, Bash) and a security-conscious mindset. Strong service orientation and clear communication. BONUS IF YOU HAVE Experience supporting a fast-growing startup. Familiarity with SaaS provisioning automation and compliance frameworks (e.g., SOC 2).