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.