Support Team Tech Lead - Remote Eligible

Support Team Tech Lead

Sentinel Blue is a values-driven Managed Security Service Provider (MSSP) committed to safeguarding our clients within the defense industrial base and broader government contracting community. Founded on trust and a relentless pursuit of excellence, our mission is to deliver scalable, comprehensive cybersecurity solutions that empower our partners to achieve long-term sustainability, regulatory compliance, and business success. The Role: Support Team Tech Lead

Sentinel Blue is looking for a Support Team Tech Lead to join our Operations team as a technical partner to the Support Team Manager. This role is for an experienced IT professional with strong technical expertise and mentoring abilities. Our ideal person for this role is a natural technical leader, skilled communicator, and deeply proficient with complex IT support scenarios and cybersecurity frameworks. This role is primarily responsible for handling the most challenging technical issues, providing technical guidance to the support team, and ensuring all solutions align with CMMC compliance requirements. The Support Team Tech Lead contributes to the technical growth of the entire support organization and has significant opportunity for advancement into senior technical leadership roles. The Tech Lead will primarily collaborate with support personnel in a mentoring capacity, but will also work directly on complex client issues and drive technical excellence across our client base.

This is a full-time position that is fully remote. Due to the nature of our work, you must be a U.S. citizen with eligibility for a clearance. No exceptions.

A day in the Support Team Tech Lead role

The Support Team Tech Lead starts the day with a standup call/check-in with the Operations team and Support Team Manager to review complex issues, team development needs, and technical priorities. They will then review and take ownership of the most challenging support tickets that require advanced technical expertise or compliance considerations. The Tech Lead will spend time mentoring team members through complex troubleshooting scenarios, providing guidance on best practices, and conducting knowledge transfer sessions. From there, they will work on strategic initiatives such as developing CMMC-compliant solution frameworks, creating technical training materials, and establishing standardized approaches for recurring complex issues. The Tech Lead will collaborate closely with the Support Team Manager on technical team development while maintaining focus on hands-on technical work. The Tech Lead will also have opportunities to work with Security Operations and vCISO teams to ensure support solutions meet enterprise security requirements.

Key Responsibilities

• Handle the most complex and challenging IT service requests, incidents, and escalations that require advanced technical expertise
• Provide technical mentoring and guidance to support team members, helping develop their troubleshooting and problem-solving skills
• Ensure all support solutions and implementations comply with CMMC requirements and cybersecurity best practices
• Develop and maintain technical documentation, standard operating procedures, and knowledge base articles focused on complex scenarios
• Lead technical training sessions and knowledge sharing initiatives to elevate the entire team's capabilities
• Collaborate with the Support Team Manager on technical skill development plans and team growth strategies
• Drive the implementation of long-term, scalable solutions rather than quick fixes
• Serve as the primary technical escalation point for challenging Microsoft 365, Active Directory, and security-related issues

What We Can Offer

Sentinel Blue is a young company with a focused mission: We're bringing enterprise-class cybersecurity to small and medium sized businesses. Frankly, we're pushing the envelope of how things are done and constantly seeking innovative ways to meet that mission. The pace is fast, and we're always learning new things. This is a great place if you want to lead technical innovation, mentor talented professionals, and build cutting-edge cybersecurity solutions. Further, success in this role can quickly transition into senior technical leadership or specialized cybersecurity roles. The right person will find themselves in a fun, dynamic environment, solving the most interesting technical challenges while developing the next generation of cybersecurity professionals.

You will be required to achieve a Security+ certification in the first 12 months of hire; we'll cover your certification costs and provide paid time for you to study!

Requirements

• U.S. citizenship
• Security+ (or higher) certification at hire or within 365 days of hire
• 5-10 years of experience in IT systems administration and technical support roles
• In-depth understanding of Microsoft ecosystem, including advanced Microsoft 365, Intune, and Azure administration
• Extensive experience with Microsoft Intune policy management, device configuration, and endpoint compliance enforcement
• Advanced knowledge of Conditional Access policy configuration, implementation, and troubleshooting
• Minimum 3+ years of hands-on experience with Government Community Cloud High (GCC High) tenant administration and compliance requirements
• Proficiency in PowerShell and Python automation scripting for system administration and process improvement
• Advanced knowledge of IT systems, including virtualization, enterprise Windows environments, endpoint management, and complex infrastructure
• Strong understanding of cybersecurity principles and CMMC compliance requirements
• Proven experience in technical mentoring or team training
• Advanced knowledge of networking, including complex DNS, DHCP, VLANs, firewall configurations, and hybrid cloud connectivity
• Ability to analyze complex technical problems, develop comprehensive solutions, and mentor others through similar scenarios
• Excellent communication skills for both technical and non-technical audiences

Preferred Qualifications

• Deep experience with CMMC framework implementation and compliance validation
• Advanced experience with Azure Government and Office 355 GCC High environments
• Strong background in cybersecurity frameworks (NIST SP 800-171, DFARS, ISO 27001, CIS Controls)
• Experience in technical leadership or mentoring roles within managed services organizations
• Advanced PowerShell scripting and automation capabilities
• Relevant advanced certifications (CISSP, CISM, Azure certifications, or similar)
• Experience developing technical training programs and documentation
• Knowledge of compliance auditing and assessment processes

Benefits

• Fully paid individual healthcare, vision and dental insurance for the employee
• Paid certification and training opportunities
• Three weeks of paid vacation + 10 paid holidays
• A supportive environment with a focus on keeping healthy work-life balance
• Retirement benefit (401k) with company match