Top Tech Jobs & Startup Jobs in Toronto

Develop Tailscale client and backend components with focus on iOS and Android. Implement cross-target shared code, unit and integration tests, support mobile VPN infrastructure, and maintain compatibility with recent and older platform versions while collaborating asynchronously on a distributed team.

Lead the dataplane product vision and roadmap to ensure secure, high-performance connectivity across clients, relays, routers, and connectors. Define customer-facing performance and reliability SLOs, drive regional capacity and relay operations, own operator UX (console and CLI), partner with engineering, GTM, and customers on production traffic commitments, and represent Tailscale externally to partners and enterprises.

Build and maintain core billing systems: integrate third-party billing platforms, implement metering/pricing/rating for subscriptions and usage, ensure accurate usage tracking, automate reconciliation and reporting, establish observability and incident response, and collaborate with product, finance, and support teams to deliver reliable billing features.

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.