Principal, Technical Support Engineer Endpoint

About the Job: As a Principal Support Engineer – Endpoint, you will serve as a senior individual contributor responsible for diagnosing and resolving complex Windows and macOS endpoint agent issues across enterprise customer environments. This role is deeply hands-on and requires extensive real-world experience working directly with endpoint agents, operating systems, and endpoint security technologies at scale. You will work closely with customers, Engineering, and QA to investigate advanced endpoint failures, reproduce issues in lab environments, identify root cause, and validate fixes. Success in this role depends on your ability to operate independently, think systematically, and execute deep technical troubleshooting across endpoint agents, operating systems, and supporting services. Job Responsibilities: Own hands-on troubleshooting and resolution of complex endpoint agent issues on Windows and macOS in enterprise customer environments, including installation, upgrades, removal, service startup, persistence, OS compatibility, performance, stability, connectivity, and configuration. Perform deep investigation of endpoint behavior using logs, telemetry, diagnostics, and OS-level tooling to identify root cause and validate fixes. Reproduce customer-reported Windows and macOS endpoint issues in lab or test environments to confirm behavior, isolate failures, and verify resolutions. Identify and resolve interoperability issues between DTEX endpoint agents and third-party endpoint or security tools (e.g., EDR, DLP, MDM). Work directly with customers to investigate and resolve advanced endpoint-focused issues in production environments. Provide supporting troubleshooting for Linux-based DTEX components that interact with endpoint deployments (services, logs, networking, configuration), with primary focus remaining on endpoint execution. Partner with Engineering and QA to report endpoint defects, validate fixes, confirm workarounds, and support root-cause analysis. Author and maintain endpoint-focused runbooks, troubleshooting guides, and internal documentation based on real customer issues and field experience. Maintain a high-fidelity lab or virtual test environment to reproduce endpoint issues, validate hypotheses, and test new endpoint features. Apply systematic troubleshooting techniques across endpoint agents, operating systems, supporting services, and data flows. Skills & Qualifications: 6+ years of deep, hands-on experience supporting Windows and macOS endpoint agents in enterprise environments. 6+ years in a senior individual contributor role such as L3 Support Engineer, Endpoint Engineer, Windows/macOS Engineer, or Security Support Engineer. Proven expertise troubleshooting endpoint agent behavior across Windows and macOS, including installation failures, upgrades, persistence, OS compatibility issues, performance degradation, and stability problems. Strong experience analyzing endpoint telemetry, logs, and diagnostics to identify root cause in complex system interactions. Demonstrated experience resolving interoperability issues between endpoint agents and security tools (EDR, DLP, MDM, or similar). Kernel-level understanding of Windows, including ETW, WFP, memory management, process/thread behavior, and driver interactions. macOS internals experience, including Endpoint Security framework, System Extensions, FSEvents, MDM interactions, notarization, code signing, and process lifecycle. Working knowledge of Linux system administration sufficient to troubleshoot supporting services that interact with endpoint deployments. Experience supporting enterprise-scale environments with large endpoint fleets. Strong written and verbal communication skills, with the ability to explain complex endpoint issues clearly to customers and internal teams. Strong time management skills and sense of urgency in customer-impacting situations. BS or MS in Computer Science, Engineering, or a related technical discipline (or equivalent practical experience). Preferred Qualifications: Experience supporting endpoint security, insider risk, UEBA, or behavioral analytics platforms. Familiarity with Elasticsearch or OpenSearch from a support or troubleshooting perspective. Experience reproducing customer issues in lab or test environments that mirror production endpoint configurations. Exposure to cloud or hybrid enterprise environments (AWS, Azure, GCP). Linux internals knowledge, including kernel/user space boundaries, eBPF, LSM (SELinux/AppArmor), cgroups and namespaces, netfilter, systemd, proc/sysfs, inotify/fanotify, auditd/seccomp, and ELF/ptrace. Experience with third-party endpoint security products such as CrowdStrike Falcon, Palo Alto Networks, or similar. Background supporting large enterprise, financial services, or government customers. Active U.S. Top Secret Security Clearance (a plus). Why Join DTEX This role is ideal for someone who wants to build, scale, and lead—bringing strong judgment, commercial instincts, and modern AI fluency to a fast‑growing cybersecurity company. Impact at Scale – Drive the growth of a market-leading cybersecurity company. Thriving Company Culture – DTEX fosters a values-driven environment prioritizing respect, inclusion, and collaboration. Growth & Development – Opportunities for professional advancement and lifelong learning. Flexibility – Hybrid or remote work options. Comprehensive Benefits – Competitive compensation, equity participation, health and wellness benefits, and generous time-off policies. About DTEX DTEX is the leader in risk-adaptive security, unifying human, data, and AI risk through a behavioral intelligence platform. Built for enterprise scale, DTEX detects threats early and prevents breaches before they impact the business. By analyzing how people, data, and AI systems interact, DTEX surfaces early indicators of risk that other tools miss and provides the context needed to act with precision. The platform brings together insider risk management, risk-adaptive data protection, user and entity behavior analytics, user activity monitoring, and AI risk management into a single, cohesive solution. Organizations and governments worldwide rely on DTEX to protect sensitive data, enable secure innovation, and safeguard trust. With privacy-by-design telemetry and adaptive controls, security teams can reduce risk without disrupting productivity. Joining DTEX means working on some of the most complex and high-impact security challenges facing enterprises today. DTEX is proud to provide equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, gender, religion, sex, national origin, age, disability, or genetics. Pursuant to the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records. Exact compensation may vary based on skills, experience, and location. Base salary range (SF Bay Area): $150K-200K