Senior IT Operations Engineer

About the Role

We run IT across a portfolio of ten companies from three-person startups to larger organizations with hundreds of contractors and accounts to administer and support and we operate as a small, senior team that punches well above its weight. This role is in the critical path of how our portfolio companies operate. When things work, CEOs and their teams move fast. When things don't, everything slows down. This is more than support. It's operations, troubleshooting, and scripting in service of businesses that need to keep moving. IT here operates as a strategic partner to the business, not a help desk function and the people on this team are expected to think that way. That means we'll bring you into context about what each company does, how they operate, and what matters to them because the best solutions come from someone who actually understands the business they're supporting, not just the tools.

As an IT Operations Engineer, you'll own problems end-to-end across identity, SaaS platforms, endpoints, and security. You'll work directly with founders, CEOs, and engineering teams sometimes in the same day. You'll know when a situation calls for rigor and process, and when it calls for just getting something done by Tuesday. You'll reach for an AI tool or write a quick script when that's the fastest path to a real solution.

If you've spent your career in IT and never once thought to build something yourself, this probably isn't the right role. But if you're the kind of person who automates things that annoy you, gets curious about how systems actually work, and genuinely enjoys helping people who are stressed and under pressure we'd love to talk.

The Environment

• Ten portfolio companies, ranging from three-person startups to larger organizations with hundreds of contractors and accounts each at a different stage, with different needs and different levels of structure
• Cloud-first, SaaS-native stack no legacy infrastructure, no on-prem drama
• Small IT team you'll have real ownership and direct visibility into decisions, not a layer of managers between you and the work
• Fully remote we operate asynchronously across time zones, but also move fast when something needs to move fast. Strong written communication and self-direction are non-negotiable.
• Active M&A environment we stand up IT for new entities and manage migrations when companies are divested. You'll see work here that most IT roles never touch.

What You'll Own

Cross-Portfolio Support

• Serve as a primary technical resource across the portfolio, handling escalated issues that require real judgment not just a runbook
• Adapt your approach to each company's size and maturity: a 3-person startup and a larger org with hundreds of accounts need different energy and different solutions
• Own the full laptop lifecycle across the portfolio procurement, provisioning, MDM enrollment, and ongoing endpoint management
• Research technology options and put together recommended paths forward when a CEO or stakeholder has a problem that doesn't have an obvious solution over time, you'll have increasing autonomy to make those calls independently
• Collaborate directly and proactively with engineering teams not as an escalation path, but as a natural part of how you work when problems cross into platform or DevOps territory

Identity & Access Management

• Make sure the right people have access to the right things and that the wrong people don't. That means owning onboarding, offboarding, and role changes across every company in the portfolio
• Be the person who gets called when someone can't get in, has too much access, or needs something changed fast
• Manage RBAC, SSO, and SCIM provisioning across platforms JumpCloud is our primary identity provider
• Troubleshoot authentication issues across our SaaS stack and keep access changes aligned with least-privilege without making it harder for people to do their jobs

SaaS Platform Administration

• Administer and troubleshoot our core platforms: Google Workspace, JumpCloud, Slack, CrowdStrike, Halo ITSM, and the SaaS tools integrated across the portfolio
• Own platform configuration, integration troubleshooting, and access reliability
• Be the person who actually understands how these systems talk to each other

Operational Improvement

• When you see something broken or repetitive, fix it don't just log it
• Write and maintain documentation and runbooks that actually get used
• Build small automations and scripts when the manual alternative is a waste of everyone's time
• Bring ideas to the team; this is a small group and good thinking gets acted on

What We're Looking For

Experience

• 2–4 years in IT operations, systems support, or a similar role in a SaaS-forward environment
• Hands-on experience with identity platforms JumpCloud, Okta, Azure AD, or similar
• Solid understanding of SSO protocols (SAML, OAuth, OpenID Connect) and SCIM provisioning
• Experience with RBAC and access governance in practice, not just in theory

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• Comfortable supporting both macOS and Windows endpoints “(90% Mac, and you’ll do your work in a Mac environment).”
• Comfort reading and writing basic scripts in Python, Bash, or PowerShell you don't need to be a developer, but you should have built something at some point, even if just for yourself

The Profile

• You use AI tools (Claude, ChatGPT, or similar) as a natural part of how you work for troubleshooting, documentation, scripting, navigating uncertainty, and problem solving
• You communicate well with non-technical people, especially under pressure. Founders and executives should feel better after talking to you, not more stressed.
• You can work independently and manage your own priorities without needing to be told what to do next
• You're comfortable in ambiguity different companies, different problems, different contexts every week
• You know when to apply process and when to just solve the problem

Nice to Have

• Experience with CrowdStrike, Slack, Google Workspace, Halo ITSM, or similar platforms
• Exposure to M&A-related IT work entity setup, migrations, divestitures
• Familiarity with scripting in Python, Bash, or PowerShell
• Experience supporting multiple companies or clients simultaneously

Working Hours & Async Expectations

This role is fully remote. We primarily work asynchronously, but there is a firm expectation that you are available and responsive during U.S. Eastern business hours. You should be comfortable making decisions independently, communicating proactively when something needs attention, and not waiting to be asked.

What Success Looks Like

Six months in, the CEOs and founders across our portfolio know your name and look forward to talking to you. The most repetitive problems you inherited are either automated or documented out of existence. When something breaks, you own it you don't route it. When something crosses into engineering territory, you don't stop at the edge; you walk across and figure it out together.