Developer Advocate

About Tailscale

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. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.

Job Description

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.

Key Responsibilities

• 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. Strong judgment is essential.
• Know what deserves depth, what should be left out, and how to explain complex technical ideas without oversimplifying or skipping the hard parts.
• Ship consistently, with an expectation of producing high-quality videos on a regular, fast-paced cadence.
• Comfortably explain nuanced technical concepts directly to developers, writing your own demos or examples where appropriate.
• Maintain a calm, credible presence that builds trust over time. Coding experience is desirable and familiarity with developer tooling is essential.
• Step into our established YouTube presence as part of our Developer Relations team and help refine and evolve Tailscale’s video strategy, formats, and voice.
• Represent Tailscale publicly through conference talks and in-person events as a steward of the brand.

What We Are Looking For

Video and post-production

• Demonstrated experience creating long-form, technically focused video content for developer audiences and beyond.
• Ability to explain systems and trade-offs clearly without oversimplifying or relying on hype.
• 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.
• Demonstrated editorial judgment in selecting topics, calibrating depth, and prioritizing clarity over exhaustive coverage when appropriate.
• 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).
• Help capture and amplify technical talks, live demos, and community interactions as needed.
• Surface developer stories and use cases that illustrate how people use Tailscale in the real world.

Qualifications

• 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.io, etc.), 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.
• Ability to manage multiple workstreams and meet regular publishing deadlines.
• 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.

Nice to Have

• 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).

What We Offer

• An inclusive, flexible environment where you can be your authentic self.
• A competitive total compensation package, including base salary, an equity incentive plan and variable commission (for quota-based roles).
• Comprehensive group benefits with no waiting period for you and your family.
• Remote first company—most of our teams work fully remotely. Enjoy flexibility, participate in virtual and in-person social events, and leverage our corporate co-working program.
• Connect with other Tailscalars IRL at our annual company retreat, team off-sites, and collaborate in person with teammates across Canada, the United States, and the United Kingdom.
• Support for your personal and professional development with $1500 USD annually for professional development, mentorship, coaching, and internal promotion opportunities.
• Paid time off and a healthy work-life integration through our flexible program.
• A build-your-own home office setup, including a company-owned laptop (Mac or PC), monthly home internet reimbursement, and $1000 USD to customize your workstation.
• Generous parental leave program from your first day.

Key skills/competency

• Video Production
• Technical Content Creation
• Developer Advocacy
• Video Editing
• Content Strategy
• Public Speaking
• Networking Concepts
• Developer Tooling
• Audience Engagement
• Scripting & Demos