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Salary: CAD 215,740 - 269,340 / annual
Tailscale is seeking an experienced Manager of Developer Relations Engineering to lead a team of technical builders who help developers discover, understand, adopt, and build with Tailscale's secure networking platform. This is a player-coach role combining team leadership with hands-on technical execution.
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. You'll lead the 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.
Key responsibilities include:
- Leading Tailscale's Developer Relations Engineering team and roadmap, translating company, product, and developer priorities into focused technical projects and programs
- Managing and developing a high-performing team of Developer Relations Engineers, setting clear expectations, providing meaningful technical ownership, and coaching both senior and developing talent
- Leading the team in building high-quality technical experiences including integrations, example applications, open-source projects, demos, workshops, reference architectures, and tutorials
- Identifying and personally contributing to high-leverage technical projects (player-coach: comfortable with IDE, prototyping, code review, debugging, and demo creation)
- Serving as a visible technical voice for Tailscale through videos, presentations, demos, integrations, workshops, and community engagement
- Ensuring DevRel work is technically accurate, engaging, relevant, and aligned with product positioning
- Partnering closely with Product, Engineering, Growth, Content, Sales, and Customer Success to coordinate launches and educational initiatives
- Influencing product strategy by identifying developer workflows and ecosystem opportunities
- Defining, tracking, and reporting on DevRel performance metrics including audience growth, engagement, product activation, integration adoption, and self-serve funnel contribution
- Using qualitative developer insight and performance data to prioritize programs and demonstrate DevRel investment value
Tailscale is a fully distributed, venture-backed company (backed by Accel, CRV, Insight, Heavybit, and Uncork Capital) founded in 2019. The company delivers software that makes it easy to securely interconnect people and their devices, protecting networks and sharing access to internal tools for teams of every size.
REQUIREMENTS:
- 6+ years of relevant experience in Developer Relations, developer advocacy, engineering, or related field
- 2+ years of experience managing, coaching, or leading technical contributors and scaling a DevRel or similar function
- Strong software engineering foundation with comfort 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—from idea through launch and iteration
- Ability to translate product and company priorities into a focused technical roadmap for a small team with thoughtful trade-offs
- Strong program management skills including planning, prioritization, delegation, and proactive risk communication
- Strong developer-product instincts and ability to recognize where developers are stuck and whether solutions require product changes, integrations, tools, examples, tutorials, or explanations
- Strong written and verbal communication skills with ability to explain complex technical concepts clearly and engagingly
- Experience 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 GitHub workflows, pull requests, issue discussions, and collaborating with external developers
- Experience defining and reporting on DevRel metrics, program performance, or contribution to product and business outcomes
- Comfortable operating in ambiguous, fast-moving environments and creating clarity through direct communication and documented plans
- Low ego, high horsepower with collaborative mindset
- Must have tried and used Tailscale
NICE TO HAVE:
- Experience leading DevRel for developer-focused infrastructure, networking, security, or open-source products
- 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 in fast-paced startup or scale-up environments
About Tailscale
AI / Data / Infrastructure; SaaS / Enterprise Software — secure networking platform built on WireGuard.
