IT Systems Engineer

Cacheflow; San Francisco (CA); On-site; USD 190,000 - 240,000; Full time

Job summary

Cacheflow is seeking a Systems Engineer to establish AI-powered internal tools and enhance corporate security. You will manage the SaaS stack including Okta and Google Workspace while improving the overall security posture of the company.

The ideal candidate has over 4 years in systems engineering, deep expertise in macOS, and proficiency in automation scripting. The role promises a competitive salary range between $190,000 and $240,000 USD.

Qualifications

• 4+ years in systems engineering, corporate IT, or hybrid IT/security role, ideally at a startup.
• Deep macOS fluency including shell/Python scripting and hands-on MDM troubleshooting.
• Okta administration skills covering lifecycle management and device trust policies.

Responsibilities

• Own and evolve corporate IT infrastructure and SaaS stack management.
• Operate and mature MDM stack and enforce device trust policies.
• Build and maintain internal MCP servers and design automation tools.

Skills

macOS fluency

Python scripting

MDM experience (Rippling, Jamf, Kandji)

Okta administration

Automation scripting

SaaS stack management

AI tools proficiency

Job description

Kikoff: The Fintech Powering Financial Security at Scale

Kikoff is a profitable, pre‑IPO fintech company on a mission to empower everyone to achieve financial security. With record revenue growth in 2025 and a unicorn valuation, we've built a suite of products that help millions of people build credit, access liquidity, and save money.
We're scaling fast. Join us if you want to build something meaningful and help millions of people move forward financially.

Why Kikoff:

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.

The role

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.

What you'll own

• 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

What we’re looking for

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

Base Range: $190,000 — $240,000 USD

Equal Employment Opportunity Statement

Kikoff Inc. is an equal opportunity employer. We are committed to complying with all federal, state, and local laws providing equal employment opportunities and considers qualified applicants without regard to race, color, religion, creed, gender, national origin, age, disability, veteran status, marital status, pregnancy, sex, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.

Please reference the following for more information.