Top Tech Jobs & Startup Jobs in Toronto

Own the full new-business sales cycle from prospecting through closed-won deals. Generate approximately one-third of the pipeline, manage inbound leads, engage senior technical buyers, educate prospects, and build customer trust. Analyze market and customer trends, organize sales activities and forecasts in Gong and Salesforce, support customers across time zones, and represent Tailscale at local and industry events. The role is hybrid in Toronto, requiring three in-office days per week.

Manage and expand existing customer accounts through upsells, renewals, product education, adoption support, forecasting, and revenue delivery. Build pipeline, develop mutual success plans, and present to senior stakeholders. Collaborate with Solutions Engineering, Customer Success, Support, Marketing, and Product teams. The role requires quota attainment, technical or developer-product sales experience, and participation in recorded customer meetings. It is hybrid in Toronto, requiring three in-office days weekly.

Manage and expand existing customer accounts through upsells, renewals, product education, adoption support, forecasting, and mutual success planning. Build pipeline, own account revenue targets, and collaborate with Solutions Engineering, Customer Success, Support, Marketing, and Product. The role requires customer presentations, opportunity management, quota attainment, and participation in recorded meetings. It is hybrid in Toronto with three in-office days per week.

Own the vision, strategy, and roadmap for Tailscale’s networking features, including App Connectors, DNS, Funnel, and Tailscale Services. Lead operator experience across the admin console and CLI, translate complex networking systems into intuitive product surfaces, partner with go-to-market and customer-facing teams, and develop customer insights across users ranging from homelab operators to large enterprises. Drive end-to-end product ownership, from strategy and requirements through launch, measurement, and iteration.

Own the vision, strategy, and roadmap for Tailscale’s Identity portfolio, including authentication, authorization, lifecycle management, SSO, SCIM, access policies, and user management. Lead operator and end-user experiences across the admin console, API, and clients. Partner with engineering, product, design, and customers to prioritize improvements and deliver secure, intuitive identity capabilities for developers, administrators, and enterprises.

Manage and mentor software engineering teams across multiple product pods. Provide technical direction, guide design decisions, oversee production services and incident response, and drive planning across short- and long-term horizons. Responsibilities include recruiting, performance management, career development, cross-functional collaboration, engineering culture, operational reliability, and fostering inclusive, psychologically safe teams in a fully remote startup environment.

Own and improve Tailscale’s software release management process, including release cadence, readiness criteria, rollout coordination, go/no-go decisions, tooling, documentation, and operational metrics. Partner with engineering, product, TPM, and support teams to identify risks, coordinate planning, keep releases on schedule, and drive scalable process improvements.

Develop and implement security and privacy improvements across Tailscale’s codebase. Audit features for vulnerabilities, conduct threat modeling and security analysis, drive mitigations, and promote secure coding practices through guidance and training. The role spends at least half its time writing software and requires expertise in application security, web and API vulnerabilities, cryptography, networking protocols, and platform development.

Build and maintain core billing software, including subscription and usage-based pricing, metering, rating, reconciliation, reporting, and third-party billing integrations. Design distributed, event-driven systems, ensure data integrity and observability, support billing incidents, and collaborate with product, finance, sales, and support teams. Provide technical leadership, participate in architecture reviews, mentor engineers, and own features throughout the product lifecycle.

Owns Tailscale’s Product operations model, including roadmap health, launch readiness, documentation, onboarding, feature requests, customer insight, operating rhythms, and product data strategy. Partners with Product, GTM, Support, Data, and company leadership to identify operational gaps, improve planning and prioritization, establish scalable processes, and drive alignment in a remote-first environment.