Top Tech Jobs & Startup Jobs in Calgary

Build and lead Tailscale’s internal AI enablement capabilities, including developer tools, workflows, coding-agent practices, evaluation processes, and safety guardrails. Partner with engineering and other teams to identify high-impact AI opportunities, drive adoption, measure productivity and quality outcomes, and communicate recommendations to leadership. The role requires hands-on software engineering, internal tooling, AI coding-tool expertise, strong communication, and comfort working independently amid ambiguity.

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 Tailscale’s web experimentation program across high-traffic pages. Set the roadmap, testing standards, statistical decision rules, and platform governance; design and run high-impact pricing and homepage experiments; validate tracking and results; maintain the experiment knowledge base; report findings to marketing leadership; and coach teams on hypothesis quality, test design, and interpretation. The role partners with web, development, design, product marketing, and analytics in a remote-first environment.

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.

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.

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.