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).

About DTEX
DTEX is the global leader in Workforce Cyber Intelligence & Security. Our mission is to safeguard the digital workforce by detecting and mitigating insider risks, preventing data loss, and enabling secure innovation.

We empower organizations to protect their most valuable assets – their people, their data, and their intellectual property—without compromising privacy or trust. Our solutions provide unmatched visibility and context into workforce behaviors, helping enterprises stop insider threats, achieve regulatory compliance, and accelerate digital transformation securely. Learn more about DTEX mission to proactively protect global organizations from insider threats at www.dtex.ai; LinkedIn DTEX: Overview | LinkedIn

Our ideal customers include large, security-conscious organizations across financial services, critical infrastructure, technology, defense, and healthcare—where protecting sensitive data and ensuring compliance are mission-critical.

Joining DTEX means joining a passionate team working at the intersection of cybersecurity, intelligence, and trust. Together, we’re redefining how organizations protect their future.

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

Learn more about this Employer on their Career Site

Principal, Technical Support Engineer Endpoint