Level 3:IT Support Specialist & Client Support

LEVEL3:MSP RELATIONSHIP AND PROJECT LEAD Teamswell is a high-growth nearshore outsourcing company working for US companies. Our mission is to help small and medium-sized US businesses grow and become more profitable by having access to highly engaged, skilled, and experienced talent at a fair price, and to generate career opportunities for bilingual professionals in Latin America with fair compensation and professional and personal growth opportunities. We are currently looking for a LEVEL 3 – MSP Relationship and Project Lead . This is a Systems Administrator and Client Relationship Lead position at a 30-year-old IT Managed Services Provider. 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. They are 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 your candidate can diagnose a security incident and then explain what happened to an operations manager in plain language – and leave that person feeling confident, not confused – they belong here. In Teamswell every team member has an instrumental role and impact on the success of our business and our client’s success, so we seek to have highly motivated individuals who thrive in a fast-paced work environment, who are intelligent, eager to work hard, reliable, and able to communicate effectively with all levels of an organization. Our LEVEL 3 – MSP Relationship and Project Lead will possess the skills and experience required and will also possess a positive attitude and ability to solve complex problems and work in a fast-paced and rapidly changing environment. We value people who are good communicators, quick learners, scrappy about finding creative solutions to problems, and conscious of their work quality. We expect all our team members to deliver excellence in both technical expertise as well as in their everyday relationships with their team. CORE RESPONSIBILITIES • 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. • 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 EXPERIENCE & 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. • 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.