Systems & Security Engineer

At Fairly we're revolutionizing vacation rental care:
Making life better for property owners, caretakers, and guests alike.
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Fairly runs a lean engineering team, and over the last few years we've built out a security, compliance, and IT foundation that is now mature: SOC 2 and PCI-DSS programs running on Drata, a SIEM on Datadog, unified identity and device management on Jump Cloud and Google Workspace, and automated vulnerability management across our AWS/CDK stack. These programs are well built and well run.

Your job is to carry these forward and to expand what this role can do for the company. We're looking for someone who will keep those programs strong and who is curious and driven enough to grow the role beyond them, making the company work better: digging into operational problems, building automations for what they find, handling escalations from customer support before they reach engineers, and taking a share of on-call and break/fix work.

This is a role for a generalist with a builder mentality: solid in security and IT fundamentals, and eager to keep expanding in breadth. If you're the person on every team who ends up understanding how everything connects and quietly making it better, this is probably for you.

• Keep SOC 2 and PCI-DSS in continuous good standing on Drata: monitor and remediate flagged controls, keep policies current, collect and organize evidence for auditors.
• Run the recurring compliance calendar: annual risk assessment, DR/BCP tabletop exercises, quarterly ASV scans, annual penetration test coordination and remediation tracking, PCI SAQ, and banking partner coordination.
• Provide technical evidence and answers during audit and pentest cycles, working alongside our CTO who is the auditor and vendor point of contact and the named PCI role.
• Own and improve the security tooling: SIEM detections, custom rule creation when necessary and log volume, dependency and secret scanning, security awareness training assignment, AWS and Git Hub org guardrails.

• Own day-to-day identity administration across Google Workspace, Jump Cloud, and Auth0: provisioning and deprovisioning, role grants, SaaS access requests, password and MFA resets.
• Own endpoint management: MDM and EDR configuration and compliance, device enrollment, and the security posture of our laptop fleet.
• Run the employee hardware lifecycle: procurement, imaging, shipping and receiving for hires and departures, inventory tracking.
• Field employee questions and either act to resolve issues or know where to redirect requests.
• Manage our SaaS and vendor footprint: license reviews, renewals, and vendor security reviews.

• Be the technical escalation point for customer support: when a case needs someone who can read logs, query data, trace a workflow, or fix a record, it comes to you before it reaches product or engineering.
• Take a share of on-call coverage and handle break/fix bugs and small production fixes.
• Turn recurring escalations into runbooks, tooling, or fixes so they stop recurring.

• Investigate operational problems as an analyst: pull data, find the pattern, write up what's actually going on and what to do about it.
• Build automations for the problems you see, whether that's a Claude skill, a Git Hub Action, a scheduled job, an internal tool, or a small service.
• Contribute to internal AI and agentic tooling that helps ops, support, and engineering move faster.

• Hands-on experience administering a cloud-native IT stack:
  Google Workspace, an identity provider (Jump Cloud, Okta, or similar), MDM/EDR, and SSO/SAML/OIDC integrations.
• Working familiarity…