Level 3 – System Administrator & Client Relationship Lead

Work Setup: Fully Remote Work Schedule: Monday – Friday, Pacific Standard Time Salary: $3,300 - $3,700 Role Overview The person in this role will own both the technical infrastructure and the client experience for a portfolio of customer accounts, many of whom are technologically sophisticated, cutting-edge software startups and security-conscious VC firms. This role is also the senior technical authority that clients rely on, and they need to be someone a non-technical founder trusts as much as a technical CTO respects. If you are the type who can diagnose a security incident, explain what happened to an operations manager in plain language, and leave that person feeling confident, not confused, then YOU belong here. This Role IS: The face of our company to technologically sophisticated, security-conscious clients — you own relationships, not just tickets Equal parts technical problem-solving and warm, clear client communication A Mac-first, Google Workspace-first, SaaS-security environment Autonomy with accountability — startup clients expect fast, independent judgment This Role IS NOT: A backend NOC or infrastructure role where you work silently behind the scenes A pure engineering role — if you prefer zero client contact, this is not the right fit A Windows Server / Active Directory / on-prem data center environment A role with heavy supervision and rigid escalation paths Responsibilities: Technical Delivery Own the deployment, configuration, and lifecycle management of our security tool stack (SentinelOne, Okta, Entra ID, Cynomi, KnowBe4, etc.) across client environments. Provide Tier 2 and Tier 3 support for escalated issues across Mac workstations, networks, Google Workspace, and SaaS platforms. Troubleshoot and resolve incidents independently with clear, client-readable documentation. Lead technical projects: migrations, security tool rollouts, network upgrades, compliance implementations. Develop process automation to reduce repetitive manual work (not infrastructure-as-code; think workflow efficiency). Own recurring technical issues and implement long-term root-cause fixes. Support monitoring, patching (including CVE remediation alerting), and incident response workflows. Evaluate new platforms to determine their suitability as part of our tool stack. Perform system updates, backups, and security audits. Client Experience Serve as the primary technical point of contact for assigned client accounts. You own the relationship, not just the ticket queue. Translate complex technical concepts into clear, confident language for non-technical stakeholders (startup founders, ops managers, office managers). Lead client-facing project presentations: scoping, status updates, and post-implementation reviews. Collaborate with Tier 1 and Tier 2 team members to share knowledge and elevate the team's client communication standards. Bridge the gap between subject matter experts and end-users – ensure that SOPs, documentation, and client-facing instructions are user-friendly and accessible. Identify opportunities to improve service delivery and proactively communicate them to clients and internal leadership. Contribute to and improve knowledge base documentation with a client-readability lens. Required Qualifications Technical Qualifications 10+ years of experience in IT support, systems administration, and security project implementation. Strong Mac/macOS support experience. Candidates without extensive Apple experience must obtain Apple Desktop Support certification within 90 days. Experience administering Google Workspace environments for distributed/remote teams. Strong cybersecurity literacy: hands-on experience with zero-trust SaaS security platforms (SentinelOne, Okta, Entra ID, Cisco Umbrella, KnowBe4, or equivalent). Solid networking fundamentals (VPNs, firewalls, routing), ideally supporting Cisco Meraki environments. Experience with endpoint management / MDM tools (Jamf, Intune, or similar). Demonstrated experience leading SaaS security implementation projects end-to-end: from scoping and proposal through deployment and client sign-off. Client-Facing Skills (Equally Weighted) Demonstrated experience as the primary point of contact for client accounts – not just an escalation resource, but the person the client calls first. Proven ability to explain technical issues to non-technical audiences in plain language and leave them feeling confident, not overwhelmed. Experience leading or co-leading client meetings, project kickoffs, and status reviews. High customer satisfaction scores or equivalent evidence of strong client relationships (references, testimonials, NPS). Comfort with ambiguity: startup clients often don't know what they need, and you help them figure it out. Soft Skills Ownership mindset – if it's your account, it's your problem until it's solved. Ability to work independently with minimal supervision across multiple time zones. Continuous improvement orientation: you don't just fix the ticket, you fix the system that created the ticket. Strong written communication – client-facing emails and documentation should be clear, professional, and warm.