System Administrator

Location | Napa, CA headquarters or US remote. Pacific-hours overlap preferred. You're the kind of person who thinks about what could go wrong—and fixes it before it happens. You're sharp, detail-oriented, and driven by the idea that great monitoring and proactive care prevent crises. You love solving problems before customers feel them, and you take pride in knowing that your work is keeping systems running smoothly. But lately, you might be craving a team that matches your standards—where preventing problems and driving real customer value go hand in hand. That's where Endsight comes in. Who We Are Endsight is a fast-growing IT Managed Service Provider built on one core belief: When we help others thrive, we thrive too. We partner with small and mid-sized organizations—including nonprofits—to ensure their technology performs flawlessly so they can focus on what they do best. We're a team that learns fast, leans in, and looks out for one another. Life here feels like being part of a great university—you'll grow quickly, connect deeply, and do work that truly matters. Purpose. What You will Do You will be the NOC's frontline for delivering proactive value through alert analysis and resolution. Your focus isn't just working tickets—it's analyzing alerts, identifying the real issue, and putting a resolution in motion that prevents problems from coming back. You will drive root cause fixes, reduce alert noise, and ensure escalations to customer teams are clean and clear. You will own: Triaging inbound alerts and identifying the real issue behind the signal, assessing context, severity, and business impact before taking action Resolving alerts to root cause—digging deeper than symptoms and validating that remediation steps are durable, not just a temporary fix Monitoring backups, patches, and infrastructure (servers, firewalls, storage, switches, wireless) to catch risks like disk failure, failed updates, or degraded performance before they impact customers Tuning alerts and flagging redundant or low-value signals to reduce noise and focus on what matters Preparing clean handoffs to Technical Account Managers and customer points of contact when issues require project work, procurement, or scheduling Keeping your backlog clear—no floating tickets, no lingering escalations. You know your numbers and bring insights to your 1:1s Contributing to proactive improvements in monitoring, alerting, and platform management as you grow in the role Who Thrives Here You'll fit right in if you: Take pride in helping others succeed Love mastering your tools and improving your craft Communicate clearly and stay composed under pressure Are energized by teamwork and mutual respect Want to grow in a place where your success helps everyone winQualifications Required: 2+ years of experience in IT operations, NOC support, systems monitoring, or similar role in an MSP or technical services environment Hands-on experience monitoring and responding to infrastructure alerts (servers, storage, firewalls, backups, patches, or similar) Strong understanding of Windows and Linux server environments, including patch management and backup processes Experience with one or more monitoring platforms (Ninja, N-Central, ConnectWise Manage, Datto RMM, or similar) Ability to troubleshoot infrastructure issues independently and think through root cause rather than surface-level fixes Clear communication skills, both with technical team members and when explaining issues to non-technical stakeholders Strong time management and ability to prioritize alerts based on severity and business impact Willingness to follow standard work, document findings, and contribute to continuous improvement of monitoring and alerting Preferred: Experience with infrastructure as code or automation (PowerShell, Python, or similar) Familiarity with cloud platforms (Azure, AWS) and hybrid infrastructure management Background in proactive maintenance and preventive monitoring rather than reactive ticket-only work Experience managing Pods or accounts with multiple customer environments Exposure to ITIL framework or similar structured IT service delivery methodology Hands-on experience with Datto or similar backup platforms Join a Team That is All-In on Helping You Thrive If you're ready to perform at a high level, learn like crazy, and make a real impact for the people you serve—Endsight is where you belong. Apply today and let's build something excellent together. Benefits. What You will Get Medical: Company pays 100% of the base plan for the employee and family Dental & Vision 401(k) with employer matching Accrued Paid Time Off 9 Paid Holidays Career Development support and programs