FileCloud is looking for a highly skilled Senior Systems Software Engineer to join our team. You will work on the core sync and OS integration layer of FileCloud Desktop. Your primary focus will be system-level development on Windows using modern C++ (C++17 and higher) and a strong understanding of Windows internals, filesystems, and OS integration. You will design and implement core sync and filesystem logic, integrate with Explorer, and collaborate closely with QA and UI teams. The role requires someone who can work independently in a remote environment and take ownership of complex technical areas.

About the Product & Company:

FileCloud is a hyper-secure EFSS (enterprise file sync and share) platform that provides industry leading compliance, data governance, data leak protection, data retention and digital rights management capabilities. FileCloud is a leader in content governance and collaboration for unstructured data, trusted and used worldwide across Global 1000 enterprises, educational institutions, government organizations, and service providers. In addition to its enterprise file sharing solution, FileCloud’s product portfolio also includes Signority (acquired in May 2024), a Canadian-based e-signature and document workflow platform. We are currently expanding our team as we grow and improve FileCloud.

Key Responsibilities:

• Design, implement, and maintain system-level components for FileCloud Desktop on Windows in modern C++ (C++17 and higher).
• Work with Win32/WinRT, the Windows Cloud Files API (CFAPI), and our custom driver to handle filesystem events, placeholders, hydration/dehydration, and user actions.
• Implement and maintain gRPC services and clients (and JSON/REST-style APIs where applicable) that connect system components to higher-level layers (Electron/TypeScript UI, server-side services).
• If you have macOS experience, contribute to macOS system components in Swift using Apple File Provider and Endpoint Security/ESClient.
• Develop and maintain unit tests (gtest) and integration tests (Python + pytest) to build and extend automated coverage.
• Integrate with File Explorer for overlays, context menus, and other shell extensions, including COM where needed.
• Use tools like Visual Studio, WinDbg, and Procmon to debug complex issues in production-like environments.
• Contribute to build and CI/CD pipelines (e.g., Jenkins, WiX for installers, vcpkg for dependencies, PowerShell scripts where helpful).
• Strong commercial experience with modern C++ (C++17 and higher).
• Solid knowledge of Windows internals: processes, C++ threading primitives (e.g. std::thread, std::mutex), synchronization, I/O, memory, security.
• Hands-on experience with Win32 APIs and willingness to work with WinRT as needed.
• Experience with multithreaded and asynchronous code.

Key Skills & Experience:

Modern C++ / Windows system programming

• Strong commercial experience with modern C++ (C++17 and higher).
• Solid knowledge of Windows internals: processes, C++ threading primitives (e.g. std::thread, std::mutex), synchronization, I/O, memory, security.
• Hands-on experience with Win32 APIs and willingness to work with WinRT as needed.
• Experience with multithreaded and asynchronous code.

Filesystems, sync & networking

• Good understanding of filesystem behavior: notifications, caching, metadata, locking, renames, symlinks/junctions.
• Experience in or strong interest in sync/backup clients, cloud storage, or related areas.
• Familiarity with networked applications (HTTP/HTTPS, TLS, proxies) from a developer perspective.

APIs, testing & debugging

• Experience with RPC / typed APIs (e.g. gRPC, JSON/REST, or similar) and willingness to work with gRPC daily.
• Hands-on experience writing automated tests: unit tests in gtest and integration tests in Python + pytest.
• Strong debugging skills on Windows using Visual Studio and system tools (WinDbg, Procmon, logs).

Collaboration & work style

• Ability to work independently and take ownership of complex subsystems.
• Comfortable collaborating with UI (Electron/TypeScript/Vue), QA, and backend engineers.
• Good communication skills in English and prior experience in a remote or distributed team.

Nice-to-have / Learn-on-the-job

• Experience with the Windows Cloud Files API (CFAPI) or other virtual filesystem/sync APIs.
• Experience building installers with the WiX Toolset.
• Familiarity with vcpkg for C++ dependency management.
• Experience with COM APIs for shell integration.
• macOS system development in Swift using Apple File Provider and Endpoint Security/ESClient.
• Experience with Jenkins or similar CI systems.
• Scripting skills in PowerShell (and/or basic shell scripting on macOS/Linux).
• Background in cloud storage, sync clients, security/endpoint products, or distributed systems.
• Awareness of security best practices when working at the OS and filesystem layer.

If you meet most of the core requirements but not everything on the “nice-to-have” list, we still encourage you to apply.

What We Offer

• Be part of a team of passionate, committed individuals dedicated to building a world-class product
• Dedicated time for training and education opportunities
• A mentorship model wherein your mentor and team support your development
• A competitive salary with an annual bonus
• Fully remote working whilst offering flexible hours that fall outside of the companywide core hours of 9am -12pm (US Eastern Standard Time)
• 20 days of paid time off which increases by a further 2 days after 3 years of service and 3 days after 5 years of service (in addition to 10 public holidays in your country)
• Paid day off on your birthday or on an alternative day if your birthday falls outside a normal working day
• Paid day off to volunteer with the charity of your choice
• Paid monthly internet cost, as well as lunch and wellbeing stipend provided
• Reimbursement of all hardware costs associated with the role

Please note that we conduct background security checks for everyone joining our team.