Senior/ Principal Support Engineer

Responsibilities Serve as the endpoint subject-matter expert for support by reviewing customer configurations, controls, and policies and making prioritized recommendations. Critique Reach’s endpoint findings and distinguish urgent, meaningful issues from noise. Troubleshoot Reach integrations with third-party endpoint and security products, including EDR, DLP, and MDM tools. Diagnose complex customer issues end to end using logs, telemetry, diagnostics, and OS-level reasoning, then provide reproducible diagnoses and proposed fixes to Engineering. Enable Sales Engineering teams to interpret endpoint findings, defend recommendations, and translate product output into customer impact. Support Customer Success as a deep technical resolver for difficult endpoint-related problems. Partner with Engineering and QA to report defects, validate fixes, confirm workarounds, and drive root-cause analysis. Own escalations, reproduce and test issues, document solutions, and maintain runbooks and troubleshooting guides. Maintain lab or test capabilities for validating endpoint behavior and integration edge cases. Requirements At least 6 years of deep, hands-on experience with Windows and macOS endpoint agents and enterprise endpoint security. Experience in a senior individual-contributor role such as L3 Support Engineer, Endpoint Engineer, Windows/macOS Engineer, or Security Support Engineer. Strong knowledge of endpoint agent installation, upgrades, persistence, OS compatibility, performance, and stability across Windows and macOS. Kernel-level understanding of Windows, including ETW, WFP, memory management, process and thread behavior, and driver interactions. Experience with macOS Endpoint Security, System Extensions, FSEvents, MDM interactions, notarization, code signing, and process lifecycle. Track record of analyzing endpoint telemetry, logs, and diagnostics to identify root causes in complex system interactions. Experience resolving interoperability issues between endpoint agents and EDR, DLP, MDM, or similar security tools. Working knowledge of Linux system administration and experience with enterprise-scale environments and large endpoint fleets. Ability to prioritize endpoint findings and controls and clearly explain their importance to customers, Sales Engineering, and Engineering. Strong written and verbal communication, time management, urgency, systems thinking, and root-cause investigation skills. Bachelor’s or master’s degree in Computer Science, Engineering, or a related technical discipline, or equivalent practical experience. Familiarity with identity and IdP troubleshooting, SSO, SAML/OIDC, conditional access, endpoint threats and vulnerabilities, and email security controls is valued. Experience supporting endpoint security, insider risk, or behavioral-analytics platforms is preferred. Experience reproducing customer issues in production-like endpoint labs and exposure to AWS, Azure, or GCP are preferred. Familiarity with Linux internals and third-party endpoint security products such as CrowdStrike Falcon, Microsoft Defender, or SentinelOne is preferred. Benefits Competitive salary and equity package. Medical, dental, and vision insurance, including options with company-paid employee coverage. FSA, HSA, and 401(k) plans. Company-paid life insurance and disability coverage with buy-up options. Voluntary pet insurance, identity theft coverage, and legal services. Unlimited PTO and sick time.