Staff IT Engineer

About Us:Treeline is building a comprehensive software stack to transform traditional Managed Service Providers — firms that handle ongoing IT, security, and a majority of software purchasing for small and mid-market businesses—into a software-defined model powered by automation and AI. Valued at more than $150 billion, the MSP market comprises 45,000 providers across the U.S. and Canada, serving the majority of SMB and mid-market enterprises. Founded by Stanford alumni with over a decade of experience in Silicon Valley, Treeline is backed by top VC firms.We’re a small, highly effective team that values impactful execution, modern tooling, and minimal bureaucracy. We prioritize making Treeline a truly enjoyable, long-term workplace—one where communication is open, politics are absent, and engineers have the autonomy and support to tackle challenging problems. What You’ll Do:Own end-to-end service delivery for Treeline customers — serving as the senior technical authority across endpoint strategy (macOS, Windows, mobile), endpoint management (Fleet), identity (Okta), endpoint security (CrowdStrike), network access (Tailscale, Twingate, Zscaler, or similar), collaboration administration (Google Workspace, Slack, and similar), and digital workplace (Google Meet, Zoom, or similar)Lead complex customer onboarding and environment migrations: inherit existing IT environments, assess tooling gaps, design the target architecture, and execute the transition to Treeline's platform with minimal disruption to the customer's operationsDrive automation adoption in customer environments — identifying manual workflows, partnering with Treeline's Automation team to build replacements, and championing the shift from reactive support to proactive, software-defined service deliveryServe as the primary technical escalation point: triage and resolve high-severity incidents, manage vendor relationships on behalf of customers, and ensure SLA compliance across all service commitmentsContribute to Treeline's playbook library: document environment-specific runbooks, integration patterns, and operational procedures that make every customer environment reproducible and every IT scenario teachableYou Might Thrive at Treeline If You:Have outgrown reactive IT and want to work in an environment where the goal is to make yourself obsolete through automation — you measure success in tickets eliminated, not tickets resolvedThink at the customer-environment level, not the individual-ticket level: you see the whole architecture, understand the dependencies, and build solutions that hold up at scaleAre genuinely curious about how AI changes the role of IT — you see it evolving as a true business enablerTake mentorship seriously: you remember what it was like to be junior, you build up the people around you, and you measure your success partly by how good your team getsAre motivated by ownership and accountability: you don't want someone else to sign off on your architecture decisions or script your customer conversationsAre energized by a company in motion, where the processes you build this quarter are the baseline next quarter — not the ceilingYour Background Might Look Something Like This:5–8 years of progressive IT engineering experience, including time in managed services, or a multi-customer/subsidiary IT role where you owned environments end-to-endDeep hands-on administration experience across Okta, Fleet MDM, CrowdStrike, and similar best-in-class IT platformsStrong foundation in network access and security architecture: Tailscale or similar ZTNA, DNS management, firewall policy, and the ability to design a zero-trust network environment from scratchAbility to lead customer-facing technical conversations at the director+ level — you can translate a device compliance posture into a boardroom-ready risk narrativeExperience owning and communicating through high-severity incidents — you've written the postmortem, managed the customer conversation, and come back with the systemic fixScripting and automation experience in Python, Bash, or a workflow tool (Workato, Make) — enough to build the bridge between \"this should be automated\" and \"here's the working workflow\"Why Join Treeline:Founding equity at an a16z-backed company entering a major public launch—you're joining at the inflection point, with a real stake in what gets builtDirect line to leadership and engineering team — your customer patterns inform the product roadmap, and your operational insights shape how Treeline scalesA clearly defined path to technical leadership: as Treeline acquires MSPs and grows its customer base, the Senior IT Engineer is the template for scaleA team that rewards people who build things better than they found them, document what they know, and bring the people around them up with them