Systems & Security Engineer

Fairly is revolutionizing vacation rental care for property owners, caretakers, and guests. The company is seeking a Systems & Security Engineer to maintain and expand its security, compliance, IT, identity, and endpoint programs while investigating operational issues, building automations, supporting escalations, and participating in on-call and break/fix work.

Responsibilities:

• 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 GitHub org guardrails
• Own day-to-day identity administration across Google Workspace, JumpCloud, 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 GitHub 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

Requirements:

• Hands-on experience administering a cloud-native IT stack: Google Workspace, an identity provider (JumpCloud, Okta, or similar), MDM/EDR, and SSO/SAML/OIDC integrations
• Working familiarity with a compliance framework in practice (SOC 2, PCI-DSS, ISO 27001, or similar), ideally on a platform like Drata or Vanta, and comfort talking to auditors
• Experience using AI coding assistants and agents as a daily part of your work, and interest in pushing how far they can go
• Enough engineering to be dangerous: you can read and write code (TypeScript, Python, or similar), work in git, query SQL, read logs and traces, and ship a working automation on your own
• Comfort with AWS and infrastructure-as-code at the level of understanding what's deployed and why, and making careful changes
• A support instinct: patience with people, urgency with problems, and the judgment to know when something needs an engineer versus when you can handle it
• Curiosity that doesn't stop at the edge of your job description, and a track record of expanding your scope wherever you've been
• Strong written communication. Much of this job is explaining what happened and what to do next
• Familiarity with Datadog, or the drive to get deep in it quickly
• Portland or Remote
• Prior exposure to PCI-DSS specifically, or to running a small company's security program end to end
• Familiarity with Auth0, Intercom, Linear, or Snowflake
• A history of being the "systems person" at a small company: the one who figured out how everything connects and made it better