Top Tech Jobs & Startup Jobs

Own Tailscale’s web experimentation program across high-traffic pages, setting the roadmap, testing standards, governance, and decision rules. Design and run high-impact experiments, particularly for pricing and the homepage, validate measurement quality, maintain the experiment knowledge base, report insights to marketing leadership, and coach cross-functional contributors. The role requires strong experimentation statistics, web development skills, analytics proficiency, and the judgment to determine when testing is appropriate.

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.

Partner with Account Executives on enterprise sales cycles by leading technical discovery, architecture, demos, proofs of concept, security reviews, and early adoption. Design secure Tailscale solutions for hybrid, multi-cloud, and on-premises environments, advise networking and security stakeholders, support pipeline and quota outcomes, and provide customer feedback to Product, Engineering, and go-to-market teams. Occasional travel of approximately 10–20% is required.

Own the full new-business sales cycle from prospecting through closed-won deals. Generate pipeline through inbound leads and self-sourced opportunities, educate prospective customers, build trust, manage forecasts in Gong and Salesforce, and support customers across time zones. Attend and organize industry events, analyze market trends, and help develop Tailscale’s startup sales playbook. The role is hybrid in Vancouver, requiring three days per week in the office.

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.

Expand and renew existing customer accounts through upsells, adoption, forecasting, and pipeline management. The role involves educating customers on product features, creating mutual success plans, presenting to senior stakeholders, and partnering with Solutions Engineering, Customer Success, Support, Marketing, and Product. The position requires managing multiple opportunities, meeting quota, and participating in recorded customer meetings. It is based in Vancouver with three required in-office days per week.

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.

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.

Develop and maintain Tailscale’s open-source client and backend networking software. Design, test, document, and optimize networking components, distributed systems, and overlay routing features. Own services through observability, incident response, and customer escalations while collaborating with product managers and designers. Apply security-first practices and improve system efficiency, scalability, and stability in a fully remote, asynchronous startup environment.

Manage and expand existing customer accounts through upsells and renewals. Build pipeline, forecast revenue, educate customers on product features, drive adoption, and create mutual success plans. Partner with Solutions Engineering, Customer Success, Support, Marketing, and Product teams while presenting to senior stakeholders and managing multiple opportunities to quota attainment.