Opportunities in Canada

Thank you for considering Tailscale. If this job description resonates with you, please apply.  Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. We encourage you to help us break that statistic! 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 an experienced Manager, Developer Relations Engineering to lead a team of technical builders who help developers discover, understand, adopt, and build with Tailscale. You will be accountable for turning Tailscale’s technology into compelling developer experiences—from integrations and example applications to demos, tutorials, open-source projects, and technical content—that drive meaningful developer and business outcomes. This is a player-coach engineering leadership role that combines team leadership with hands-on technical execution. You’ll lead Tailscale’s Developer Relations Engineering team while continuing to build yourself: developing integrations, demos, example applications, technical prototypes, workshops, and educational experiences that show developers what is possible with Tailscale. You’ll help the team identify the highest-leverage developer problems to solve and turn successful experiments into repeatable programs. This role partners closely with Product, Engineering, Growth, Content, Sales, Customer Success, and the broader Marketing team. You’ll maintain a clear technical roadmap for the team, surface developer friction and emerging use cases back into the product organization, and build the systems and measurement practices needed to understand which DevRel investments are driving adoption. We’re looking for someone with strong engineering and technical credibility, excellent product judgment, and a track record of turning developer insight into technical experiences and projects that make complex products easier to understand and adopt. Key Responsibilities Lead Tailscale’s Developer Relations Engineering team and roadmap, translating company, product, and developer priorities into a focused set of technical projects and programs. Manage and develop a high-performing team of Developer Relations Engineers. Set clear expectations, give team members meaningful technical ownership, provide strong coaching and feedback, and help both senior and developing talent increase their impact. Lead the team in building high-quality technical experiences including integrations, example applications, open-source projects, demos, workshops, reference architectures, tutorials, and other developer tooling that helps developers quickly understand what they can build with Tailscale. Identify and personally contribute to high-leverage technical projects. This is a player-coach role: you should be comfortable opening an IDE, building a prototype, reviewing code, debugging an integration, or creating a working demo alongside the team. Serve as a visible technical voice for Tailscale through hands-on work such as videos, presentations, demos, integrations, workshops, and community engagement.  Ensure DevRel eng work is technically accurate, engaging, relevant to its intended audience, and aligned with current product positioning Partner closely with Product, Engineering, Growth, Content, Sales, and Customer Success to coordinate launches, educational initiatives, and developer feedback. Influence product strategy by identifying developer workflows and ecosystem opportunities where Tailscale can create differentiated value, and work with Product and Engineering leaders to validate and prioritize those opportunities. Act as the senior DevRel partner for major launches and strategic bets. Define, track, and regularly report on DevRel eng performance, including audience growth, engagement, product activation, integration adoption, and contribution to the self-serve funnel Use qualitative developer insight and performance data to prioritize programs, improve execution, and demonstrate the value of DevRel eng investments What We Are Looking For 6+ years of relevant experience in Developer Relations, developer advocacy, engineering, or a related field 2+ years of experience managing, coaching, or leading technical contributors and scaling a DevRel or similar function.  Strong software engineering foundation. You should be comfortable writing and reviewing production-quality code, working with APIs and developer tooling, debugging technical problems, and getting hands-on with unfamiliar technologies. Experience building developer-facing technical projects such as integrations, SDK examples, reference applications, open-source tools, demos, workshops, or developer infrastructure—and taking them from idea through launch and iteration. Ability to translate product and company priorities into a focused technical roadmap for a small team, and to make thoughtful trade-offs between experimentation, developer education, integrations, and other projects. Strong program management skills, including planning, prioritization, delegation, and proactive risk communication Strong developer-product instincts and the ability to recognize where developers are getting stuck, what will create an “aha” moment, and whether the right solution is a product change, integration, tool, example, tutorial, or explanation. Strong written and verbal communication skills, including the ability to explain complex technical concepts clearly and engagingly Experience with and joy for collaborating cross-functionally with Product, Engineering, Marketing, Growth, Sales, or Customer Success teams Ability to balance hands-on execution with team leadership and long-term program development Experience working in public codebases and developer ecosystems, including comfort with GitHub workflows, pull requests, issue discussions, technical feedback, and collaborating with external developers. Experience defining and reporting on DevRel eng metrics, program performance, or contribution to product and business outcomes Comfortable operating in an ambiguous, fast-moving environment and creating clarity through direct communication and documented plans Low ego, high horsepower with a “yes, and” mindset to collaboration You have tried and used Tailscale Nice to Have Experience leading DevRel for a developer-focused infrastructure, networking, security, or open-source product Deep familiarity with Tailscale, WireGuard, networking concepts, identity-based access, or Zero Trust architecture Experience supporting product-led growth or self-serve adoption Experience building technical integrations, example applications, community tools, or open-source projects Established experience speaking at conferences, hosting technical videos, or facilitating developer workshops Experience developing new public-facing technical voices within a team or company Familiarity with measuring developer journeys from content engagement through signup, activation, and paid conversion Experience managing agency partners, contractors, program budgets, or external contributors Experience working in a fast-paced startup or scale-up environment 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 $215,740 — $269,340 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 .