Lead IT Systems Engineer

We're hiring an experienced Lead IT Systems Engineer to be the senior technical owner of Obsidian's identity, endpoint, and IT platform foundation, and to help us operate that foundation as code. You will own how identity flows from our HR system into Okta and out to every application, how our device fleet is managed and hardened, and how the configuration behind all of it lives as version-controlled, AI- and human-authored code. You will set the bar for how a modern, security-first IT organization runs in an AI-forward company.

This is a high-leverage seat at a pivotal moment. Our identity platform is being stood up with a lifecycle orchestration layer in front of it, and we are moving the whole stack onto an infrastructure-as-code operating model. We are looking for a senior technical owner to set the bar for identity architecture, configuration-as-code, AI-augmented operations, and how a lean IT function leverages AI and automation to grow the function.

You will report directly to the VP of Business Systems, Data & IT. You will partner closely with Security, DevOps, HR, Finance, and the go-to-market teams, and you will have an opportunity to lead a lean team across the Business Systems, Data & IT function.

What You'll Do

Own the identity foundation

• Serve as the senior technical owner of Okta as our primary identity provider, covering Universal Directory, SSO, MFA (Okta Verify FastPass and FIDO2), conditional access, Device Access, and Okta Identity Governance for access certifications and reporting.
• Own the lifecycle orchestration that turns HR events into access. This includes joiner, mover, and leaver flows from our HRIS through the orchestration layer into Okta, with same-hour offboarding.
• Own the SSO application catalog across our estate of applications: sequence the integrations, enforce group-based access by role, and make the catalog the definition of what is sanctioned.

Operate IT as code

• Manage core platform configuration as version-controlled code in our corporate GitHub organization. This spans Okta policies, groups, group rules, app assignments, and governance campaigns; Jamf profiles, policies, and smart groups; the GitHub organization itself; and the underlying Google Cloud foundation, using OpenTofu and Terraform.
• Bring imperative surfaces under the same discipline. Manage Google Workspace through scripts in git, run keyless through Workload Identity Federation, with verification and drift reporting where true state management is not possible.

Set the standard for AI-augmented operations

• Author configuration with AI assistance from the start. You will set the team standard for what good looks like here.
• Use read-only tooling for live observability, drift triage, and log investigation, with humans gating every production change.
• Build AI-assisted IT support and self-service workflows on our automation platform so routine requests for access, provisioning, and license changes resolve without a ticket queue and a manual handoff.

Automate and harden the fleet

• Own endpoint management across platforms with device trust and assurance wired into access policies, automated third-party patching, and application allowlisting.
• Advance zero-trust network access and secrets-management patterns so identity and device health decide access.

Raise the bar across IT

• Set technical standards for the IT function, document them so they scale beyond your own hands, mentor teammates, and be the person others learn identity and automation from.
• Partner with the VP to shape IT priorities and sequencing, and represent IT's requirements in cross-functional security, compliance, and platform decisions.

What You'll Bring

We know few candidates match every line below. If you own most of the required list and are excited by the rest, we want to hear from you.

Requirements:

• 8 or more years building and operating IT systems, identity, or platform infrastructure in production, with clear ownership of the systems you ran.
• Deep, hands-on Okta ownership across SSO, MFA, Universal Directory, Lifecycle Management, and conditional access, ideally including Identity Governance. You have owned an Okta tenant end to end.
• Hands-on Jamf Pro expertise managing a production Mac fleet, including configuration profiles, policies, smart groups, and patch workflows.
• Proven infrastructure-as-code ownership with Terraform or OpenTofu managing real infrastructure or SaaS configuration in production, shipped through a pull-request-based GitOps workflow such as GitHub Actions.
• Daily use of AI coding tools to ship production work.
• Hands-on MDM depth with Jamf or Intune at fleet scale, including device compliance and trust.
• Scripting fluency in Python, PowerShell, or a comparable language, and comfort automating against SaaS and platform APIs.
• Clear written and verbal communication. You can explain an access policy or automation decision to an engineer and to a business stakeholder with equal clarity.

Preferred

• Experience with a lifecycle or identity-governance orchestration layer and with HRIS-driven provisioning (Rippling, Workday, or similar).
• Google Workspace administration at scale, including GAM7.
• Secrets and non-human credential management (HashiCorp Vault, Doppler, Secret Manager, or equivalent).
• Workflow and integration automation on an iPaaS or agent platform such as Workato, including human-in-the-loop steps and MCP-style tooling.
• Zero-trust network access (Jamf Connect, Zscaler, Tailscale, or similar) and enterprise browser deployments.
• Exposure to compliance-driven controls and evidence automation for SOC 2 or ISO 27001 and 27701, and tooling such as Drata.
• Google Cloud Platform and familiarity with agentic or MCP tooling for operations.
• B2B SaaS or cybersecurity domain background.