Top Tech Jobs & Startup Jobs in Montreal

Build and maintain Tailscale's native Windows client using C#, XAML, and WinUI/Windows App SDK. Implement platform integrations and UI components, ensure compatibility across Windows versions, write unit and integration tests with Microsoft Testing Platform v2 and xUnit, and contribute to cross-platform client and backend code (including Go). Collaborate asynchronously within a distributed team and iterate quickly in a startup environment.

Provide Tier 2 technical support and escalations for Tailscale customers, troubleshoot complex networking and SSO issues, manage ticket SLAs, mentor Tier 1, collaborate with Product/Engineering, and drive improvements to user experience while maintaining high CSAT.

Work on an AI-native Strategic Projects team to turn prototypes (LLM gateways, proxies, sandboxes) into production-grade services. Focus on hardening, observability, security review, operational tooling, customer integrations, and closing long-tail bugs and failure modes to ensure reliability and maintainability.

Build and maintain backend services for Tailscale's control plane and identity systems. Implement sign-on features (SSO, OAuth2, OIDC, SAML, WebAuthn), SCIM sync, and observable, secure, scalable services. Participate in design, testing, incident response, on-call rotation, and product decision-making alongside product and design teams.

Partner with Account Executives to drive Commercial new business by leading technical discovery, solution architecture, demos, and POCs; guide complex multi-stakeholder deals; provide product and GTM feedback; and build scalable enablement resources, demo environments, and solution blueprints for the SE team.

Design, build, test, and document core networking components across client and backend services. Improve efficiency, scalability, and stability of networking systems, own running services (observability, incidents, support escalations), and collaborate on product ideation with designers and PMs while applying a security-first mindset.

Own and improve developer experience by building demos, sample apps, docs, talks, workshops, and tools; represent Tailscale at events; collaborate cross-functionally to reduce developer friction; contribute to open source and public developer conversations; define and drive developer experience from first touch to production.

Lead frontend architecture and platform work for a unified web console: design app structure, cross-origin auth and session infrastructure, shared UI/platform abstractions, testing strategy, developer workflows, and tooling. Collaborate with product, design, growth, and infrastructure teams, provide technical leadership, mentor engineers, and participate in on-call rotation.

Manage a small senior engineering team to turn AI, identity, and networking signals into shippable prototypes, reference architectures, and customer integrations. Coach use of LLMs and coding agents while enforcing security and quality, partner with CSO/PM/customers, hire and grow the team, and coordinate cross-functional work to drive adoption and roadmap influence.

Build and maintain internal engineering services and automation to support product teams. Improve observability, CI/CD, infrastructure as code, and cloud-managed services. Own running services, participate in incident response, collaborate cross-functionally, and drive reliability, scalability, and efficiency improvements.