Top Tech Jobs & Startup Jobs in Toronto

Drive product positioning, messaging, and go-to-market for Tailscale by collaborating with product, sales, and marketing. Launch features, create sales enablement content, perform competitive analysis, represent PMM at events, and measure pipeline and revenue impact.

Designs and implements security controls across cloud platforms, operating systems, Kubernetes, networks, and CI/CD. Audits infrastructure for vulnerabilities, develops security and privacy improvements, performs threat modeling, and drives remediation. The role includes software development, infrastructure security analysis, and serving as an infrastructure-level subject matter expert during security incidents.

Own brand design projects from concept through delivery across web, campaigns, events, social media, presentations, product marketing, and internal communications. Extend visual identity, build reusable templates and design systems, present concepts, incorporate feedback, and manage multiple priorities. Collaborate with marketing, content, product marketing, web, developers, and other designers to deliver polished, consistent creative assets.

Provide Tier 1 technical support by resolving configuration and networking issues, managing a high-volume ticket queue, meeting response and resolution targets, and maintaining strong customer satisfaction. Troubleshoot across macOS, Windows, Linux, and mobile operating systems, explain technical concepts clearly, and collaborate with Customer Experience, Product, and Engineering teams to identify recurring user issues and improve the customer experience.

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.

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.

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.