Top Tech Jobs & Startup Jobs in Toronto

Build and evolve Tailscale’s customer-facing documentation platform, including docs-as-code tooling, content publishing pipelines, API documentation, search, and integrations with engineering and product systems. Implement designs, improve performance and scalability, support contributors through GitHub, automate documentation workflows, and research emerging documentation and LLM trends. The role requires full-stack development with TypeScript, JavaScript, React, Python, HTML, CSS, CI/CD, testing, and scripting.

Develop and scale integrated account-based marketing campaigns for Enterprise and Mid-Market audiences. Own strategy, audience segmentation, messaging, paid LinkedIn advertising, personalized landing pages, direct mail, gifting, Sales outreach, and performance optimization. Partner with Sales, GTM Operations, Product Marketing, Content, Events, and Partner Marketing to drive account engagement, meetings, pipeline creation, and progression.

Build and lead the frontend architecture for Tailscale’s next-generation web console. Responsibilities include developing shared frontend infrastructure, cross-origin authentication and session systems, testing strategies, unified product experiences, developer tooling, deployment workflows, and accessible UI patterns. The role partners across design, growth, infrastructure, and engineering, provides technical leadership and mentoring, and participates in an on-call rotation.

Design growth-focused product experiences across activation, onboarding, monetization, expansion, and referrals. Develop experiment concepts, prototypes, and minimum-viable solutions; collaborate with product managers, researchers, and engineers; interpret experiment results; and advocate for user-centered improvements while maintaining high design quality.

Lead technology and integration partnerships from opportunity identification through technical discovery, solution design, commercial alignment, launch, and adoption. Collaborate with partners, customers, Product, Engineering, Sales, Legal, Finance, Marketing, and Customer Success. Evaluate APIs, architectures, authentication, security requirements, and data flows while developing business cases, negotiating agreements, and influencing cross-functional stakeholders. Focus areas include PAM, VPN, AI, security, identity, infrastructure, developer tools, and related technologies.

Leads Tailscale’s global communications function, including product, corporate, internal, executive, crisis, international, and media communications. Builds narratives for technical products, develops journalist and emerging-media relationships, supports executive thought leadership, and manages awards and recognition programs. The role hires and develops a communications team, oversees agencies, partners cross-functionally on sensitive issues, and establishes scalable communications processes and measurement.

Own and improve operational processes across Engineering, Product, and Design, including bug tracking, incidents, reliability, escalations, planning, reviews, dashboards, and retrospectives. Analyze operational health data, identify trends and process gaps, communicate actionable insights, and implement improvements. The role requires hands-on execution, cross-functional coordination, technical engineering knowledge, comfort with ambiguity, and independent work in a remote startup environment.

Build and operate infrastructure and core software components supporting Tailscale’s product and internal teams. Responsibilities include improving observability, CI/CD, cloud infrastructure, managed services, Kubernetes operations, scalability, stability, and automation. The role includes incident response, customer support escalations, cross-functional collaboration, documentation, and end-to-end ownership of infrastructure projects in a fully remote startup environment.

Own and negotiate commercial agreements, advise Sales and business teams on deal structure and risk, and develop scalable contracting processes. Partner with Security, Privacy, Product, Engineering, Finance, and Operations on technology transactions, data protection, AI, pricing, and revenue matters. Support international transactions, improve negotiation efficiency through metrics and processes, coordinate outside counsel, and contribute to the growth of Tailscale’s commercial legal function.

Leads and builds Tailscale’s global legal function, advising executives and cross-functional teams on corporate governance, product, privacy, data, AI, security, intellectual property, employment, commercial, compliance, and international matters. Establishes legal strategy, processes, systems, and risk frameworks; hires and develops legal staff; manages outside counsel; supports strategic partnerships and corporate initiatives; and translates complex legal and regulatory issues into practical business guidance.