2 days ago
Remote, CanadaMid Level
Responsibilities
- Own and improve the developer experience across Tailscale’s expanding product portfolio.
- Build, debug, and ship technical projects, sample applications, demos, tools, and open source contributions.
- Create developer-facing documentation, tutorials, blog posts, videos, talks, workshops, and other educational content.
- Investigate APIs, GitHub issues, networking edge cases, and technical systems, then explain findings clearly to developers.
- Present to technical audiences through conferences, meetups, livestreams, workshops, podcasts, videos, and internal forums.
- Work publicly through GitHub issues, pull requests, community forums, social channels, and open source projects.
- Translate developer friction and feedback into better documentation, APIs, examples, workflows, and product experiences.
- Collaborate with engineering, product, marketing, support, community, and other technical stakeholders while managing multiple workstreams and event or launch deadlines.
- Travel for events, conferences, and community activities as needed.
Requirements
- Strong software engineering fundamentals and demonstrated experience building, debugging, and shipping real projects through professional work, open source, self-directed learning, or personal projects.
- Ability to create clear developer-facing materials including code samples, demos, tutorials, documentation, blog posts, videos, talks, and workshops.
- Deep curiosity about systems including networking, infrastructure, security, identity, cloud, open source, AI, and developer tooling.
- A track record of building and explaining technical systems such as production software, developer tools, infrastructure projects, homelabs, local AI setups, networking experiments, or open source contributions.
- Excellent written, verbal, and visual communication skills with the ability to explain complex technical ideas clearly, creatively, and practically.
- Experience presenting to technical audiences and working publicly through developer and open source communities.
- Strong developer empathy, emotional intelligence, product sense, cross-functional collaboration, and independent project execution.
- Bachelor’s degree in Computer Science, Computer Engineering, Electrical Engineering, or a related technical field, or equivalent practical experience.
- Preferred experience with Go, networking, VPNs, WireGuard, identity, access controls, infrastructure automation, or security products.
- Preferred experience building developer education programs, sample applications, workshops, technical video content, or conference talks.
- Preferred familiarity with secure AI access, privileged access management, zero trust, modern infrastructure security patterns, and open source contribution workflows.
Benefits
- Remote-first and flexible work environment with virtual and in-person social events and access to a corporate coworking program.
- Base salary range of $170,180–$188,940 CAD for Canada, plus equity and variable commission where applicable.
- Comprehensive health, vision, dental, and other group benefits with no waiting period.
- Employer retirement contributions matching employee contributions dollar-for-dollar up to a maximum annual employer contribution equal to 0.75% of eligible compensation.
- Annual company retreat, team off-sites, and supported in-person collaboration across Canada, the United States, the United Kingdom, and Singapore.
- $1,500 USD annually for professional development plus mentorship, coaching, and internal promotion opportunities.
- Flexible paid time off program.
- Company-owned laptop choice between Mac or PC, monthly home internet reimbursement, and $500 USD for workstation customization.
- Paid parental leave of 20 weeks for birthing parents and 16 weeks for non-birthing parents.
Tech Stack
Categories
Solutions Engineering
About Tailscale
Tailscale builds a software-defined mesh VPN that lets individuals and organizations securely connect devices and services using WireGuard and single sign-on. It sells a subscription SaaS with free and paid plans, offering features like access control lists, device authentication, and admin tooling for teams and enterprises. Founded in 2019 and headquartered in Toronto, the company is privately held and used from hobby projects to corporate networks.