Top Tech Jobs & Startup Jobs in Montreal

Develop and maintain open-source client code and backend services focused on networking features. Design, test, document, and optimize distributed networking components, improve scalability and stability, support observability and incident response, handle customer escalations, and apply security-first engineering practices. Collaborate asynchronously with engineers, product managers, and UX/UI designers throughout the product lifecycle.

Manage and mentor multiple small engineering pods to deliver and operate high-availability production services. Provide technical direction, lead incident response and on-call rotations, hire and grow the team, and collaborate cross-functionally with product and design to drive short- and long-term planning.

Develop and operate Tailscale’s control plane, relay infrastructure, identity integrations, open-source client code, and backend services. Responsibilities include designing, testing, documenting, and scaling software; improving observability, stability, and efficiency; participating in incident response; handling customer escalations; and applying security-first practices. The role also involves collaborating with designers and product managers, contributing to product strategy, and working independently in a fully distributed 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.

Owns revenue-team onboarding and ongoing enablement programs from pre-boarding through continuous development. Responsibilities include designing role-specific learning paths, managing program logistics and LMS content, partnering with sales leaders and cross-functional teams, measuring ramp and competency outcomes, and improving programs using data and feedback. The role also pilots AI-powered learning tools in a remote-first environment.

Build and maintain production-grade dbt data models and pipelines across ingestion, transformation, and visualization. Partner with Finance, Engineering, Sales, Product, and Marketing to deliver reliable data for reporting and decision-making. Improve manual workflows, validate data accuracy, and design scalable solutions using modern data modeling practices. Support financial and revenue-related analytics, including ARR and revenue recognition, while balancing immediate fixes with long-term architecture.

Lead Tailscale’s Developer Relations Engineering team, roadmap, and technical programs. Build integrations, demos, example applications, open-source projects, workshops, tutorials, and developer tooling while remaining hands-on with coding and technical problem-solving. Partner cross-functionally to improve product adoption, surface developer feedback, support launches, and measure DevRel impact. Coach technical contributors, prioritize investments, and translate complex networking and security capabilities into compelling developer experiences.

Design, build, test, document, and optimize Tailscale’s client-side networking software. Develop connectivity features for clients, subnet routers, exit nodes, and customer integrations using networking protocols and security-focused engineering. Diagnose complex network issues, support customer escalations, collaborate with product and engineering teams, contribute to open-source projects, and improve software scalability, reliability, performance, and maintainability across platforms.

Source and engage exceptional talent across technical and business functions, including Engineering, Product, Design, GTM, and G&A. Develop targeted sourcing strategies, conduct talent research and market mapping, engage passive candidates through personalized outreach, assess pipeline health, and build inclusive candidate pipelines. Collaborate with Talent Acquisition Partners and hiring teams while improving sourcing tools, workflows, data quality, automation, and AI-enabled practices.