IT Systems Engineer

This is a consumer fintech startup, and you will be working with serial entrepreneurs who have built strong consumer brands and innovative products. We value extreme ownership, clear communication, a strong sense of craftsmanship, and the desire to create lasting work and work relationships. Yes, you can build an exciting business AND have real-life real-customer impact.

Kikoff is hiring its first dedicated Systems Engineer. This isn't an IT support role — you'll be standing up AI-powered internal tooling (MCP, agents), owning our corporate identity foundation, and improving our overall corporate security. You'll work directly with the engineering and security teams.

• Corporate IT infrastructure — own and evolve our SaaS stack (Okta, Google Workspace, Slack). Procurement, provisioning, and lifecycle management
• Identity & device trust — operate and mature our MDM stack (Rippling/Jamf/Kandji), enforce Okta Device Trust policies, and ensure endpoints meet our security baseline
• MCP servers & AI agents — build and maintain internal MCP servers; design agents that automate internal ops and extend what the security and engineering teams can do
• Endpoint hardening & macOS/Windows fleet management — configuration profiles, CIS benchmark enforcement, macOS scripting, software deployment, and patch management
• Security automation — turn manual security tasks into automated workflows: access reviews, alert triage, onboarding/offboarding, posture checks

Must-have

• 4+ years in systems engineering, corporate IT, or a hybrid IT/security role — ideally at a startup
• Deep macOS fluency: shell/Python scripting, configuration profiles, and hands-on MDM troubleshooting
• Hands-on MDM experience (i.e., Rippling, Jamf, Kandji) — enrollment, policies, smart groups, zero-touch provisioning
• Okta administration: lifecycle management, device trust policies, group rules
• Proficient in scripting and building software — bash and Python at minimum. Expected to own automation scripts and internal tooling.
• SaaS stack management: tool inventory, vendor renewals, access governance
• Proficient using AI tools (Claude, Cursor, Codex or similar) as part of your daily workflow

Strong plus

• Experience building or operating MCP servers or LLM agents
• Familiarity with security concepts: least privilege, zero trust endpoint posture, log forwarding, DLP basics
• Exposure to AWS IAM or cloud infrastructure
• Experience with device trust architectures (Okta Device Trust, CrowdStrike, or similar)
• Built internal tooling from scratch — provisioning workflows, self-service automations, or agent-driven ops