Top Tech Jobs & Startup Jobs in Montreal

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.

Build and maintain internal AI enablement tools, workflows, and guardrails to help engineers use coding agents and LLMs safely. Evaluate models, partner with teams to apply AI, track adoption and impact, and provide documentation, coaching, and advocacy to increase engineering velocity.

Design, build, test, and document Tailscale's client-side networking software. Enhance connectivity between clients, subnet routers, and exit nodes. Diagnose and resolve complex customer network escalations, optimize performance and reliability, collaborate with product and engineering, adopt security-centric designs, and engage with the open-source community.

Design and implement security controls across cloud, OS, Kubernetes, networks, and CI/CD. Audit infrastructure, perform threat modeling, remediate vulnerabilities, and write software for security features and defenses.

Design and implement security and privacy features across Tailscale's codebase. Audit features for vulnerabilities, perform threat modeling and security analysis, drive mitigations to resolution, and spend significant time writing secure software (50%+ coding). Collaborate with engineering teams to promote secure coding and provide guidance and training.

Create technically accurate, growth-focused educational content (tutorials, guides, demos, comparisons) that helps enterprise and developer audiences discover, evaluate, and adopt Tailscale. Monitor communities and search signals, collaborate with product and engineering, optimize existing content, and build an AI-first program to drive self-serve revenue and product adoption.

Serve as the technical lead for strategic customers: onboard, train, troubleshoot, and drive adoption of Tailscale. Build relationships, conduct QBRs, recommend best practices, escalate product feedback, and maintain customer-facing documentation to enable long-term success and expansion.

Execute and QA marketing campaigns: build landing pages and emails, manage a 500k+ newsletter, coordinate webinars, maintain marketing automation/CRM workflows, pull performance reports, and document repeatable processes to scale operations.

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.

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.