Developer Advocate H/F

Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We're building a future for the Internet that's easy, sensible, and safe, like it used to be. Tailscale is looking for a Developer Advocate who specializes in all aspects of the production of technically led, long-form, educational, and inspirational video content. This role is focused on creating clear, engaging videos that help developers understand not just how Tailscale works, but why it works the way it does and how those decisions affect the solutions they build.
You’ll be expected to own large chunks of the production lifecycle of our video output, from identifying which topics are worth a developer’s time to scripting, recording, editing, publishing, and measuring impact. You will know what deserves depth, what should be left out, and how to explain complex technical ideas without oversimplifying or skipping the hard parts. This role requires shipping consistently, with an expectation of producing high-quality videos on a regular, fast-paced cadence.
You should be comfortable explaining nuanced technical concepts directly to developers, writing your own demos or examples where appropriate, and maintaining a calm, credible presence that builds trust over time. Coding experience is desirable and familiarity with developer tooling is essential.
Initially, you’ll step into our established YouTube presence as part of our Developer Relations team, and over time, you’ll help refine and evolve Tailscale’s video strategy, formats, and voice. Video and post-production

Demonstrated experience creating long-form, technically focused video content for developer audiences and beyond
Ability to independently own most of the video production lifecycle, from topic selection and framing through scripting, recording (camera, audio, and screen capture), editing, and post-production
Proven ability to ship consistently on a regular cadence without sacrificing quality
Familiarity with and demonstrable experience of using audience signals (retention, feedback, comments, usage patterns) to refine future content
Technical Fluency and Product Understanding

Strong understanding of where Tailscale fits in its ecosystem and how we are making connectivity easier for developers across broad spectrums of the industry
Familiarity with developer tooling, workflows, and environments
Comfort learning and reasoning about technical systems well enough to explain why they work the way they do
Ability to write or adapt demos, examples, or walkthroughs that support video content
Experience working with or around open-source, networking, infrastructure, homelab, self-hosting, or distributed systems is a plus, but not required.
Curiosity and willingness to dig into unfamiliar technical areas in order to teach them accurately
Developer Relations Support

Support DevRel during events, conferences, and community moments (up to 20% travel).
As needed, help capture and amplify technical talks, live demos, and community interactions.
Surface developer stories and use cases that illustrate how people use Tailscale in the real world.
1–3+ years experience creating technical, educational, or developer-focused content (video, talks, tutorials, or similar)

• Hands-on experience with video production tools and workflows (Adobe Suite, Final Cut Pro, frame.including scripting or outlining, recording, and editing long-form content
• Strong written and verbal communication skills, with the ability to explain technical concepts clearly and accurately
• Comfort learning technical concepts related to developer tooling, infrastructure, or networking in order to create educational content
• Comfortable presenting on camera and explaining technical ideas to a developer audience
• Familiarity with video performance metrics (e.g., watch time, retention, engagement) and using feedback to iterate on content
• Collaborative mindset, with experience working alongside engineers, product managers, or other technical stakeholders
• Willingness to participate in public-facing work such as videos, talks, or occasional in-person events

Prior experience in Developer Relations, technical education, or developer marketing
Basic familiarity with programming or scripting (e.g., Go, JavaScript, Python) or a demonstrated willingness to learn
Experience contributing to or maintaining a public content portfolio (YouTube channel, blog, talks, or similar)
Tailscale's compensation package includes base salary, equity, and comprehensive benefits. 136,680—$171,520 CAD
We encourage you to help us break that statistic!
An inclusive, flexible environment where you can be your authentic self. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).
Take advantage of coverage for health, vision, dental, and more for you and your family!
Remote first company —most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.
Attend our annual company retreat, participate in team/department off-sites, or use your individual travel budget to meet up with team members in Canada, the US, or the UK.
Support for your personal and professional development. Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!
A build-your-own home office setup. Generous parental leave program from your first day. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups for up to 26 weeks.