MyWorkDrive empowers enterprises with secure remote file sharing, enabling access to on-premises and cloud storage file servers via mapped drives, web browsers, or mobile clients — without the need for a VPN.
Position Overview
We are expanding our Support and QA teams and seeking a seasoned, remote IT professional/Systems Administrator to serve as a Level 3 Senior Support Engineer for enterprise customers. In this role, you will handle the most complex escalations, support hybrid identity and storage deployments, and ensure seamless integration between on-premises Windows/AD environments and Microsoft cloud services.
You will combine mastery of Windows identity and Microsoft cloud (Entra ID, Azure Files/Blob, SharePoint, Graph, Intune, SAML) with a strong customer-first mindset—treating every customer issue as our problem to solve.
Schedule * Full-time, Monday to Friday 9-6 Pacific time, with flexibility for occasional off-hours support for critical incidents or maintenance windows.
Key Responsibilities
Customer Support & Troubleshooting * Act as the senior escalation point for complex issues related to Active Directory, Entra ID (Azure AD), ADFS, SMB, Kerberos, NTLM, and Windows identity. * Assist IT Administrator customers with installation, configuration, and advanced troubleshooting of MyWorkDrive products in diverse Windows Server, Active Directory, and Azure environments. * Diagnose and resolve authentication and authorization issues involving Azure Files, Azure Blob, SharePoint, Enterprise Apps, SAML SSO, and Graph API permissions. * Understand unique client use cases and challenges to design solutions that ensure compatibility, performance, and security across hybrid environments. * Maintain detailed documentation of customer environments, troubleshooting steps, and resolutions in helpdesk and knowledge base systems.
Quality Assurance & Testing * Build and manage test environments using Hyper-V, Azure, and representative customer configurations, including complex AD and Entra ID topologies. * Reproduce and isolate defects, perform rigorous QA testing, and file clear bug reports for development, including identity, SSO, and file access scenarios. * Validate fixes and new features related to Windows authentication (Kerberos/Interactive Logon), SAML, and Microsoft 365 integrations before general release.
Cross-Functional Collaboration * Engage with a global customer base via email, helpdesk, and web meetings (Teams, Zoom) to resolve escalated issues and guide best practices. * Collaborate closely with engineering, product, and sales teams to manage critical support cases, drive continuous product improvements, and assist with pre-sales technical consultations as needed.
Customer Service Mindset * Model a customer-first culture: your problem is our problem—no disdain, blame, or defensiveness toward customers. * Stay calm, empathetic, and solutions-focused in high-pressure situations, including outages and executive-level escalations. * Proactively set expectations, communicate clearly, and follow through on all commitments until resolution is fully confirmed by the customer. * Consistently meets and strives to exceed defined SLAs for response and resolution times, ensuring customers feel prioritized and informed throughout the lifecycle of their requests.
Required Skills and Experience
Support and Communication * Exceptional customer service skills, with a calm, empathetic, and solution-focused approach to every interaction. * Comfortable working with both highly technical administrators and non-native English speakers, adapting communication style accordingly (English proficiency: Upper-Intermediate or higher) * Highly responsive, able to triage and prioritize critical issues such as service outages or security-impacting incidents. * Excellent written and verbal communication skills, including clear incident summaries, root cause explanations, and step-by-step remediation guidance.
Mindset * Demonstrated ability to quickly learn and apply complex technical and theoretical information across identity, networking, and storage. * Strong sense of ownership: you drive issues to closure, collaborate proactively, and do not “throw problems over the wall.” * Entrepreneurial, self-directed, and comfortable working in a fast-moving, distributed team environment.
Extensive IT Background * 10+ years of experience deploying and managing software in Windows Server/Active Directory and Azure environments. * 10+ years of hands-on experience in computer networking (TCP/IP, DNS, routing, firewalls, VPNs, load balancers, proxies).
Technical Mastery — Identity & Cloud * Deep knowledge of Windows client and server OS, Active Directory, Group Policy, ADFS, and Windows authentication Kerberos, Delegation, Interactive Logo. * Mastery of Microsoft Entra ID (Azure AD) including Conditional Access, Enterprise App integrations, SAML/OIDC SSO, and application proxy scenarios. * Strong experience with Azure Files, Azure Blob Storage, SharePoint Online, and NTFS/SMB permissions in hybrid file-access architectures. * Hands-on experience configuring and troubleshooting SAML/SSO, including certificate management, claims rules, and federation with third-party IdPs. * Practical experience with Microsoft Graph API permissions, app registrations, and consent (delegated and application permissions) for enterprise apps. * Familiarity with Intune device management, compliance policies, and their interaction with Entra ID and Conditional Access.
Broader Technical Proficiency * Experience with firewalls, security, switching, proxy/load balancing, Microsoft SQL, IIS, Office 365, and related enterprise tooling. * Familiarity with Android/iOS mobile devices, Azure File Storage, Active Directory Trusts, NTFS file sharing, Hyper-V, and SAML/SSO.
Education & Certification * Bachelor’s degree in Computer Science, Information Systems, or related field (preferred). * CompTIA, MCSE or related Microsoft certification (e.g., modern Microsoft 365/Azure certifications) preferred.
What We Offer * Long-term collaboration with a globally trusted enterprise software company. * Competitive compensation through a contractual cooperation model. * Fully remote work arrangements. * Opportunity to work with an experienced, international development team on a mature, enterprise-scale product.
Interested? Let’s connect and discuss the details!
