Overview

About the company

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.

Location:

Remote (US-based), working West Coast hours (must be available 9:00 a.m. – 6:00 p.m. Pacific Time)

Role Summary

MyWorkDrive is expanding its Support team and seeking a motivated remote IT professional to serve as a Level 2 Support Engineer for enterprise customers. In this role, the engineer owns support cases, answers questions for customers deploying and operating MyWorkDrive in Windows Server, Active Directory, and Entra environments, and partners with senior engineers when deeper investigation is required.

The role works directly with IT and support staff ranging from intern to CIO/CISO, helping them deploy MyWorkDrive, troubleshoot issues in deployment or production, and assist with upgrades and new features. The ideal candidate brings a strong customer-first mindset, excellent communication skills, and the judgment to know when to resolve, when to research, and when to escalate.

Key Responsibilities

Customer Support and Troubleshooting

  • Handle inbound support tickets via helpdesk, email, and web meetings such as Teams and Zoom, triaging and prioritizing based on urgency and impact.
  • Assist IT administrators with installation, configuration, and troubleshooting of MyWorkDrive products on Windows Server in Active Directory and Entra environments.
  • Provide hands-on remote support, guiding customers step by step through issue reproduction, diagnosis, resolution, and verification.
  • Follow support runbooks, flowcharts, and internal knowledge base articles to diagnose issues, while clearly distinguishing what can be resolved directly versus what should be escalated to senior engineers.
  • Collect accurate environment details including logs, configuration, and topology, document troubleshooting steps, and maintain clear records in helpdesk and knowledge base systems.

Cross-Functional Collaboration

  • Engage with a global customer base through email, helpdesk, and web meetings to resolve escalated issues and guide best practices.
  • Collaborate closely with engineering and product teams to manage critical support cases, validate defects, and drive continuous product improvement.
  • Partner with sales and pre-sales teams as needed to support evaluations, proof-of-concepts, and early-stage deployments with prospective customers.

Customer Experience and Ownership

  • Model a customer-first culture: the customer’s problem is your problem, with no blame, defensiveness, or dismissive handoffs.
  • Stay calm, empathetic, and solutions-focused in high-pressure situations, including outages and executive-level escalations.
  • Proactively set expectations, communicate frequently, and follow through on commitments until resolution is confirmed by the customer.
  • Consistently meet and strive to exceed defined SLAs for response and resolution, ensuring customers feel informed and prioritized throughout the support lifecycle.

Required Skills and Experience

Helpdesk and Enterprise Support

  • Prior helpdesk or technical support experience for enterprise software is a plus.  Not just general IT; the role supports real software products used by enterprise customers.
  • Comfortable working from support flowcharts and knowledge base articles, knowing when to answer directly, when to research internally, and when to escalate to L3 or development.
  • Demonstrated experience providing hands-on remote support rather than only collecting logs and handing off issues.
  • Able to collect information, assess the situation, and communicate clearly without over-promising or guessing; confident without being arrogant.
  • Strong written and spoken English communication skills, including the ability to draft clear meeting summaries and case updates for customers and internal stakeholders.

Mindset and Soft Skills

  • Strong willingness to learn, actively seek answers, experiment in test environments, and grow technical knowledge on the job.
  • Empathetic to customers experiencing problems and able to balance technical accuracy with approachability.
  • Operates with discipline: recommendations are based on knowledge and experience rather than guesses, and changes are validated in a lab whenever possible before production guidance is given.
  • Never over-promises, never defaults to generic actions like asking for logs without a clear reason or explicit direction from esclation, and is comfortable engaging with stakeholders from intern to CIO/CISO.

Technical Background

  • Experience with Windows Server, Windows Server networking, and cloud deployments, with an understanding of how servers, domains, and networks fit together in enterprise environments.
  • Hands-on Active Directory experience, including user and group management, permissions, and Group Policy.
  • Working knowledge of Azure and Entra ID.
  • Comfortable searching internal knowledge bases and historical support cases and applying those findings to new situations.
  • Experience with fundamental networking concepts including TCP/IP, DNS, firewalls, and VPNs sufficient to diagnose connectivity-related issues between clients, servers, and cloud resources.

Education and Certification

  • Bachelor’s degree in Computer Science, Information Systems, or a related field is preferred, but not required.
  • CompTIA, MCSE, or modern Microsoft 365 and Azure certifications are a plus.

Schedule and Work Style

  • Full-time, Monday to Friday, 9:00 a.m. – 6:00 p.m. Pacific Time, with flexibility for occasional off-hours support during critical incidents or planned maintenance windows.
  • This is a fully remote role and requires the ability to work independently, manage a support queue, and collaborate effectively across time zones through video and written communication.

Why Join MyWorkDrive

  • Help enterprises deliver simple, VPN‑free access to file servers for their users with a remote file access platform, in a space where reliability and trust really matter.
  • Join a small, highly technical team where feedback directly influences the product and where the role can grow into advanced support, infrastructure, or engineering responsibilities over time.

Candidates with enterprise software support experience, a strong desire to learn, and the soft skills to engage customers at every level, are encouraged to apply.

What We Offer

  • Long-term collaboration with a globally trusted enterprise software company.
  • Competitive compensation.
  • 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.

Email: taras.popovych@sunvery.com.ua