About Collective:

Collective is on a mission to redefine the way businesses-of-one work. Our technology and team of trusted advisors help members achieve financial independence by taking care of everything from business incorporation to accounting, bookkeeping, tax services, and access to a thriving community, all in one integrated platform. We believe in empowering self-employed people to enjoy the same tax savings that big companies get, so they can focus on their passion, not paperwork.

Featured in Forbes, Business Insider, Yahoo, Bloomberg, Financial Times, TechCrunch, and more. We are backed by General Catalyst, Sound Ventures, QED Investors, Google’s Gradient Ventures, Expa, and other investors who have financed iconic companies like YouTube, Substack, Twitch, Box, Hims, Instacart, and Lyft.

About the role:

Day to day, this is a true hybrid role: most of your time goes deep — engineering our macOS fleet, identity stack, office network, and the automation that runs our IT operations — with the rest spent working the ticket queue and helping people face-to-face.

We're a Mac shop end to end. Our stack is modern and lean, and identity sits at the center of everything: our IdP provisions most of our SaaS and our HRIS drives account lifecycle. When something breaks in that chain, you'll be the person who can trace it — not just escalate it.

What you'll do: 

• Systems engineering & automation

  • Lead the design, implementation, and maintenance of secure, scalable IT infrastructure across identity, endpoints, network, and SaaS.

  • Build and maintain automated employee-lifecycle (joiner / mover / leaver) workflows that replace manual provisioning work — automation over click-ops.

  • Contribute to our internal tooling — we script our own dashboards and automation in Python, and increasingly use AI-assisted workflows; you'll help extend them, not just consume them.

  • Serve as a technical escalation point for issues Tier 1 can't resolve, and turn recurring escalations into permanent fixes.

  Mac fleet engineering

  • Troubleshoot advanced macOS issues beyond the GUI: system logs, launch agents/daemons, configuration profiles, plists, disk and FileVault issues — comfortable living in Terminal.

  • Manage the fleet through MDM: zero-touch deployment, configuration baselines, OS update enforcement, and compliance remediation.

  • Partner with security on endpoint health — EDR sensor issues, vulnerability remediation, and closing compliance gaps.

  • Keep asset inventory accurate across procurement, assignment, repair, and decommission.

  Identity, Workspace & HRIS

  • Administer and troubleshoot our IdP: SSO/SAML app issues, SCIM provisioning to downstream SaaS, role mappings, and MFA resets.

  • Administer Google Workspace: accounts, groups, delegation, mail routing and delivery issues — including bulk and scripted admin work.

  • Trace and fix provisioning breakages across the HRIS → IdP → SaaS chain, coordinating with People Ops when data is the root cause.

  Network management

  • Manage the office network — Wi-Fi, wired LAN, VLANs, DHCP/DNS: monitor health, tune coverage and performance, and keep documentation current.

  • Troubleshoot connectivity end to end, from a user's laptop to the uplink, and own vendor and ISP escalations through resolution.

  • Keep office infrastructure running: conference-room AV and video systems, printers, and desk and peripheral deployment.

  Project execution & collaboration

  • Own IT projects end-to-end — scoping, timelines, and deliverables — and communicate status clearly to stakeholders along the way.

  • Partner cross-functionally with security, engineering, and People Ops on rollouts, integrations, and process changes.

  Service desk & customer service

  • Own tickets end-to-end in our service desk — access requests, hardware, software, lockouts, Workspace admin — with clear communication and real follow-through.

  • Deliver white-glove, face-to-face support as a primary onsite IT contact, including support for leadership and onsite events.

  • Write and maintain knowledge-base articles and runbooks so fixes stick and repeat

What you'll bring:

• 3–5 years in IT support or IT engineering, with at least 2 supporting a majority-Mac fleet.

• System administration and advanced troubleshooting across macOS endpoints, including real command-line fluency (bash/zsh — reading logs, managing services, configuration profiles, scripted fixes) and MDM platform management.

• Strong hands-on experience administering core SaaS platforms: Google Workspace, an IdP/SSO platform, MDM, and ITSM tooling.

• Working knowledge of modern identity protocols (SAML, OAuth, OIDC, SCIM) and the integrations that run across them.

• Scripting in Bash/Zsh and Python.

• Solid networking fundamentals — Wi-Fi, LAN, DHCP, DNS, VLANs — and the ability to run an office network day to day.

• Conviction that AI and automation should eliminate manual work — you build the fix once rather than click through it again.

• Excellent problem-solving and the ability to work calmly under pressure.

• Communicate effectively with engineers, security professionals, and business stakeholders — and warmly, without condescension, with the people behind the tickets.

• Ticket-queue discipline in a modern ITSM tool — you communicate status, hit SLAs, and close the loop.

What we offer:

• Hybrid Work Model: Based in San Francisco with a balance of in-office and remote flexibility.

• Fresh Lunch: Provided on in-office days.

• Commuter Support: $150 monthly reimbursement for transit expenses.

• Health & Wellness: $200 quarterly reimbursement to support your well-being.

• Time Off: Flexible PTO plus 14 company holidays.

• Comprehensive Coverage: 100% medical, dental, and vision for employees; 75% coverage for dependents.

• Parental Leave: 16 weeks fully paid.

• Retirement & Ownership: 401k plan plus an equity package.

• Team Connection: Quarterly virtual events and an annual in-person summit.