L2 Technical Support Engineer - CMMC Service Delivery; Red Cup Powered by Treeline [Remote]

Company: Red Cup

Department: Technical Services / Service Delivery

Reports To: Technical Services Manager – CMMC Service Delivery

Position Type: Full-Time

Location: Remote, U.S.-Based

Interview Requirements:  In-Person for Final Round

Position Summary

Red Cup is a managed services provider (MSP) and part of Treeline, a technology services organization spanning managed IT, cybersecurity, compliance, and advisory services. As Treeline expands its compliance business, Red Cup is building a dedicated Technical Services pod to support clients with CMMC and other regulated technology requirements.

The L2 Technical Support Engineer – CMMC Service Delivery is a hands-on technical role within this dedicated pod, responsible for resolving technical issues across endpoint, identity, cloud, networking, and security environments while operating within established security and compliance requirements.

This role requires strong technical troubleshooting skills, disciplined documentation, and the ability to work within defined security controls, access requirements, and change management processes. In regulated environments, how technical work is performed and documented is as important as resolving the issue itself.

The ideal candidate brings MSP experience, strong Microsoft and/or Google administration skills, experience supporting modern identity and endpoint environments, and an understanding of the security practices required when supporting regulated organizations.

Key Responsibilities

Technical Support & Service Delivery

• Provide Level 2 technical support across assigned clients within the CMMC Service Delivery pod.

• Troubleshoot and resolve technical issues across Microsoft 365 and/or Google Workspace, Windows and macOS endpoints, identity and access management, networking, cloud services, and security platforms.

• Manage assigned tickets through resolution while meeting established response, resolution, communication, and SLA expectations.

• Escalate complex, high-impact, or security-sensitive issues to the Technical Services Manager, L3, Engineering, or Security teams as appropriate.

• Perform user administration, device configuration, application support, access changes, troubleshooting, and other day-to-day managed services activities.

• Maintain clear, complete, and accurate ticket documentation, including troubleshooting performed, technical changes, approvals, and resolution details.

• Follow established escalation, change management, and client communication procedures.

• Identify recurring technical issues and contribute to root cause analysis and proactive remediation.

• Collaborate with L1 technicians and provide technical guidance and escalation support when needed.

CMMC & Regulated Environment Support

• Deliver technical support in accordance with client-specific CMMC, NIST SP 800-171, and other applicable security requirements.

• Follow established procedures for handling Controlled Unclassified Information (CUI) and other sensitive information.

• Adhere to client-specific access controls, authentication requirements, approved administrative tools, and secure support workflows.

• Follow least-privilege and privileged-access requirements when performing administrative activities.

• Ensure remote support, administrative access, technical changes, and troubleshooting activities are performed only through approved systems and processes.

• Maintain ticket and technical documentation capable of supporting compliance evidence and assessment requirements.

• Support remediation of vulnerabilities, technical findings, configuration issues, and control gaps as directed by the Technical Services Manager, Security, or Compliance teams.

• Assist with technical validation and evidence collection activities related to CMMC readiness and assessments.

• Immediately escalate activity, configurations, or service delivery practices that may introduce security or compliance risk.

Technical Responsibilities

• Administer and support Microsoft 365 and/or Google Workspace environments.

• Support identity and access management platforms including Entra ID and Okta.

• Support endpoint management platforms including Intune and other MDM/RMM solutions across Windows and macOS environments.

• Troubleshoot authentication, MFA, SSO, conditional access, permissions, and user access issues.

• Support endpoint security, EDR/MDR, vulnerability management, application control, and secure remote access technologies.

• Troubleshoot LAN/WAN, VPN, DNS, DHCP, wireless, and other common networking issues.

• Perform approved software deployment, patching, endpoint configuration, and remediation activities.

• Support onboarding, offboarding, access changes, and device lifecycle activities in accordance with documented security requirements.

• Execute approved technical changes while following required testing, authorization, documentation, and change control procedures.

• Participate in continuous improvement, standardization, automation, and proactive remediation initiatives.

Required Qualifications

• 3+ years of experience in IT support, managed services, systems administration, or a similar technical support environment.

• Experience working within an MSP or other fast-paced, multi-client service environment.

• Strong hands-on experience supporting Microsoft 365 and/or Google Workspace.

• Experience with identity and access management platforms such as Entra ID and Okta.

• Experience supporting Windows and macOS endpoints.

• Experience with endpoint management platforms such as Intune and other MDM/RMM solutions.

• Working knowledge of networking, endpoint security, EDR/MDR, vulnerability management, MFA, SSO, and secure remote access.

• Strong troubleshooting skills across endpoint, identity, cloud, networking, and application environments.

• Strong documentation and ticket management practices.

• Ability to follow defined technical, security, access, and change management procedures consistently.

• Strong written and verbal communication skills.

• U.S.-based and able to meet client-specific personnel, access, or data-handling

requirements associated with regulated environments.

Preferred Qualifications

• Experience supporting organizations operating under CMMC, NIST SP 800-171, DFARS, or comparable regulated security frameworks.

• Experience supporting Department of Defense contractors or organizations handling CUI.

• Experience working within CMMC Level 2 environments.

• Familiarity with Microsoft GCC/GCC High and/or Google Workspace environments used by regulated organizations.

• Experience with Entra ID, Okta, Intune, and enterprise identity and endpoint management platforms.

• Experience with SIEM/MDR, EDR, SASE, vulnerability management, application control, and privileged access technologies.

• Microsoft, Google, Okta, CompTIA, security, networking, or CMMC-related certifications.

• Experience with ConnectWise or similar PSA platforms and modern RMM tooling.

Success Measures

Success in this role will be measured by:

• SLA, response time, and resolution performance.

• Ticket quality, accuracy, and completeness of documentation.

• Technical quality and first-touch resolution where appropriate.

• Consistent adherence to security and compliance procedures.

• Appropriate handling of access, administrative privileges, and sensitive information.

• Effective escalation of complex technical issues and security or compliance risks.

• Client satisfaction and quality of communication.

• Contribution to reducing recurring issues through documentation, root cause identification, and proactive remediation.

• Readiness of service delivery records and technical evidence to support client compliance requirements.

• Ability to deliver excellent technical support while operating within the security controls required by regulated client environments.

Role Expectations

The L2 Technical Support Engineer is expected to be a strong technical contributor who can independently own and resolve a broad range of support issues while recognizing when escalation is required.

This role requires someone who is comfortable troubleshooting complex technical issues, working across multiple client environments, collaborating with other technicians and technical teams, and operating within clearly defined security and compliance processes.

In a CMMC environment, how the work is performed matters as much as whether the issue is resolved. Successful technicians will demonstrate strong technical judgment, attention to detail, disciplined documentation, respect for access controls, and a commitment to both security and exceptional client service.