Systems Operations Team Leader

We're a 30-year-old Managed Services Provider (MSP) trusted by innovative software startups, venture capital firms, and security-conscious organizations. We're looking for a senior-level Systems Administrator who thrives at the intersection of technical excellence and client leadership.

This is not a behind-the-scenes infrastructure role. You will be the trusted technical advisor for a portfolio of clients, serving as both the senior technical authority and the primary relationship owner. The ideal candidate can troubleshoot a security incident, implement a complex SaaS security solution, and then confidently explain everything to a non-technical founder in clear, understandable language.

If you're equally comfortable discussing security architecture with a CTO and guiding an operations manager through a technical challenge, we'd love to hear from you.

• Deploy, configure, and manage modern security platforms including SentinelOne, Okta, Entra ID, Cynomi, KnowBe4, and related technologies.
• Provide Tier 2 and Tier 3 support for escalated issues involving macOS, networking, Google Workspace, and SaaS applications.
• Lead technical projects from planning through completion, including migrations, security rollouts, compliance initiatives, and network upgrades.
• Troubleshoot incidents independently and document solutions clearly for both technical and non-technical audiences.
• Develop workflow automations that improve operational efficiency and reduce repetitive tasks.
• Identify root causes of recurring issues and implement long-term solutions.
• Support monitoring, patch management, vulnerability remediation, backups, system updates, and incident response activities.
• Evaluate and recommend new tools and technologies to enhance our service offerings.

• Serve as the primary technical point of contact for assigned client accounts.
• Build trusted relationships with startup founders, operations leaders, and executive stakeholders.
• Translate complex technical concepts into clear, practical business language.
• Lead client-facing meetings, project kickoffs, status updates, and post-implementation reviews.
• Proactively identify opportunities to improve client environments and service delivery.
• Create and maintain client-friendly documentation, SOPs, and knowledge base content.
• Collaborate with internal teams to elevate both technical and customer service standards.

• 10+ years of experience in IT support, systems administration, and security-focused project delivery.
• Strong hands-on experience supporting macOS environments.
• Experience administering Google Workspace for distributed and remote teams.
• Strong cybersecurity knowledge with experience managing modern SaaS security platforms such as SentinelOne, Okta, Entra ID, Cisco Umbrella, KnowBe4, or equivalent solutions.
• Solid networking fundamentals including VPNs, firewalls, routing, and wireless networking.
• Experience with Cisco Meraki environments preferred.
• Experience with endpoint management and MDM platforms such as Jamf, Intune, or similar tools.
• Proven experience leading SaaS security implementations from scoping and proposal through deployment and client sign-off.

• Experience serving as the primary contact for client accounts.
• Exceptional communication skills and the ability to explain technical issues to non-technical audiences.
• Experience leading client meetings, project reviews, and strategic discussions.
• Demonstrated ability to build trust and maintain strong client relationships.
• Comfortable navigating ambiguity and helping clients identify solutions to problems they may not fully understand themselves.

• Strong ownership mentality and accountability.
• Ability to work independently with minimal supervision.
• Continuous improvement mindset focused on solving underlying problems, not just symptoms.
• Excellent written communication and documentation skills.
• Professional, approachable, and client-focused.

To ensure a successful transition, you'll spend your first 90 days working within our Help Desk environment, learning our systems, tools, processes, and customers. After onboarding, you'll likely continue supporting the Help Desk on a part-time or rotational basis while managing your client portfolio and projects.

• You enjoy both solving technical problems and building client relationships.
• You can switch seamlessly between technical troubleshooting and executive-level communication.
• You prefer autonomy, accountability, and ownership.
• You want to make a direct impact on clients' success and security.

• You prefer a purely backend engineering or NOC position.
• You want minimal interaction with clients.
• You need constant supervision or highly structured escalation paths.
• You're looking for a traditional Windows Server / on-premises infrastructure environment.

We assess candidates on two equally important dimensions:

1. Technical Depth – Can you independently troubleshoot systems, networking, SaaS platforms, and security technologies?
2. Client Communication – Can you explain technical issues clearly and confidently to non-technical stakeholders?

Success in this role requires strength in both areas.

If you're a senior technical professional who enjoys being the trusted advisor clients rely on, we'd love to meet you.