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About Tailscale
Tailscale is making safe connection effortless 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.
About the Role
Tailscale is looking for a Developer Relations Engineer to own and improve the developer experience across Tailscale’s expanding product portfolio. You’ll help developers understand, adopt, extend, and build with our core VPN/connectivity product, while also shaping how that experience evolves as Tailscale expands into new product areas like secure AI access (Aperture), privileged access management (PAM), and whatever comes next.
You’re a builder, investigator, and storyteller. You write code, chase technical curiosities all the way down, and turn what you learn into things other developers can use like demos, docs, talks, blog posts, sample apps, workshops, videos, tools, and open source contributions. You build things, break things, explain things, and keep going until the thing you’re working on has a name.
You’re comfortable speaking at conferences and just as comfortable digging through an API, a GitHub issue, or a weird networking edge case until it makes sense. You’re probably the kind of person who runs a local AI model in your homelab and can explain exactly why. You ask “why does it work that way?” often, and your instinct is to make the answer clearer, simpler, and better for the next developer.
Requirements
- Strong software engineering fundamentals, with demonstrated experience building, debugging, and shipping real projects through professional work, open source, self-directed learning, or ambitious personal projects.
- Ability to create clear, useful developer-facing materials, including code samples, demos, tutorials, docs, blog posts, videos, talks, and workshops.
- Deep curiosity about how systems work, especially across networking, infrastructure, security, identity, cloud, open source, AI, or 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, whether through conferences, meetups, livestreams, workshops, podcasts, videos, or internal engineering forums.
- Comfortable working in public through GitHub issues, pull requests, community forums, social channels, open source projects, and developer feedback loops.
- Strong developer empathy, emotional intelligence, and product sense; you notice friction, understand why it matters, and help translate it into better docs, APIs, examples, workflows, and product experiences.
- Ability to work cross-functionally with engineering, product, marketing, support, community, and other technical stakeholders while operating independently and driving high-impact projects from idea to execution.
- Comfortable managing multiple workstreams, meeting regular publishing, event, or launch deadlines, discussing technical tradeoffs in detail, and traveling for events, conferences, and community moments.
Nice to Have
- Experience with Go, networking, VPNs, WireGuard, identity, access controls, infrastructure automation, or security products.
- Experience building developer education programs, sample apps, workshops, technical video content, or conference talks.
- A visible history of technical writing, talks, demos, open source contributions, or community work.
- Experience with homelabs, self-hosting, local AI models, infrastructure experiments, or other “I wanted to understand how this works, so I built it” projects.
- Familiarity with secure AI access, privileged access management, zero trust, or modern infrastructure security patterns.
- Familiarity with open source contribution workflows and technical collaboration in public.
Qualifications
- Bachelor’s degree in Computer Science, Computer Engineering, Electrical Engineering, or a related technical field, or equivalent practical experience.
- Strong software engineering fundamentals, whether gained through formal education, professional experience, open source work, self-directed learning, or building ambitious projects on your own.
- A track record of building and explaining technical systems. This could include production software, developer tools, infrastructure projects, open source contributions, homelab experiments, local AI setups, networking projects, or anything else that shows how you think.
- If your background is less conventional, we still want to hear from you. Bring us your GitHub repos, blog posts, diagrams, configs, talks, demos, lab notes, or the deeply specific story of why your homelab is built the way it is.
- Comfort discussing technical tradeoffs in detail such as explaining what you built, why you built it, what broke, what you learned, and what you would do differently next time.
As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale's compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire's base salary. Individual offers may vary based on experience and skill set. CAN Pay Range
$170,180 - $188,940 CAD
What We Offer
- An inclusive, flexible environment where you can be your authentic self. We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.
- A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).
- Comprehensive group benefits with no waiting period. 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.
- Employer-funded retirement contributions. Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.
- Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.
- Support for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.
- Paid time off and a healthy work-life integration. 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. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.
- Paid parental leave program. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).
Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.
Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.
Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit https://tailscale.com/scam-awareness.
