Jobs at Tailscale

Source and engage technical and specialized talent across engineering, product, design, GTM, and G&A functions. Build targeted sourcing strategies, conduct talent research and market mapping, create personalized outreach, assess passive candidates, and develop inclusive pipelines. Collaborate with Talent Acquisition Partners and hiring teams, use sourcing data to evaluate pipeline effectiveness, and improve tools, workflows, automation, and AI-enabled practices.

Coordinate recruiting processes across candidates, interviewers, hiring managers, and time zones. Manage complex scheduling, candidate communications, interview logistics, recruiting data, workflows, and documentation. Support recruiting operations, process improvements, automation, AI-enabled tools, employer branding, referrals, events, and other talent initiatives. The role emphasizes organization, proactive problem-solving, accuracy, communication, and a high-quality candidate and hiring team experience.

Own full-cycle recruiting across Engineering, Product & Design, Go-to-Market, General & Administrative, or cross-functional portfolios. Develop sourcing and recruiting strategies, assess candidates, negotiate offers, advise hiring managers, use market intelligence and recruiting data, and improve hiring processes and candidate experience in a distributed technology environment.

Leads and develops Talent Acquisition Partners, drives recruiting strategy and performance, advises senior business leaders, and uses recruiting data and market intelligence to improve hiring outcomes. The role oversees hiring across technical and business functions, supports complex searches, coaches recruiters, manages performance, and collaborates with Sourcing and Talent Acquisition Operations on scalable processes, systems, analytics, and candidate experience.

Source and engage exceptional talent across technical, product, design, GTM, G&A, leadership, and specialized searches. Develop sophisticated sourcing strategies, conduct talent mapping and market research, use pipeline data to guide hiring decisions, build inclusive talent pools, cultivate passive candidates, and ensure strong handoffs. The role also elevates sourcing capabilities through knowledge sharing, reusable research frameworks, sourcing jams, workflow improvements, analytics, automation, and AI-enabled practices.

Partner with Account Executives to drive new commercial business by leading technical discovery, solution architecture, demos, and POCs. Guide complex deals, align technical and business objectives, provide product and GTM feedback, and build scalable enablement resources, demo environments, and solution blueprints for the SE team.

Build and maintain core billing systems: integrate third-party billing platforms, implement metering/pricing/rating for subscriptions and usage-based models, ensure accurate usage tracking, observability, and high availability, automate reconciliation and reporting, collaborate with product/finance/support, lead incident response and provide technical leadership.

Drive product positioning, messaging, launches, and sales enablement for Tailscale. Conduct customer research, competitive analysis, and create collateral, demos, and enablement to generate pipeline and support revenue teams.

Designs and implements security controls across cloud platforms, operating systems, Kubernetes, networks, and CI/CD. Audits infrastructure for weaknesses, develops security and privacy improvements, performs threat modeling, and drives remediation. The role includes software development, infrastructure security, incident containment, and technical security analysis while collaborating with engineering teams in a distributed startup environment.

Provide Tier 1 technical support by resolving configuration and networking issues, managing a high-volume ticket queue, meeting response and resolution targets, maintaining strong customer satisfaction, troubleshooting across operating systems, and partnering with Customer Experience, Product, and Engineering teams to improve user outcomes.

Own brand design projects from concept through delivery across web, campaigns, events, social media, presentations, product marketing, and internal communications. Apply and evolve the visual identity, create reusable templates and design systems, collaborate cross-functionally, present concepts, incorporate feedback, and manage multiple projects while delivering polished, production-ready work.

Serve as a technical, customer-facing engineer for strategic enterprise customers: lead onboarding, provide hands-on configuration and troubleshooting, run QBRs, drive adoption and expansion, relay customer feedback to product/engineering, and produce technical documentation to enable self-service and long-term success.

Create technical, growth-focused educational content (tutorials, implementation guides, demos, comparisons) that drives discoverability and product adoption. Work with product, engineering, and marketing to build hands-on examples, optimize content for search and AI discovery, refresh existing assets, and measure impact against quarterly growth metrics.

Design and implement security and privacy improvements across Tailscales codebase. Audit features for vulnerabilities, perform threat modeling and security analysis, drive remediation, and spend at least half your time writing code to build security features, defenses, and tooling.

Own frontend architecture and platform for a unified web console. Build identity-adjacent systems (auth, sessions, CORS/CSRF protections), shared infra and tooling, testing strategies, and enable other teams to ship reliable UIs. Collaborate across design, growth, and infrastructure; participate in on-call rotation.

Design, build, and maintain internal infrastructure and shared engineering services. Improve observability, CI/CD, and automation, operate cloud-managed services and VMs, participate in incident response, and collaborate with product and customer-facing teams to enable data-driven decisions and scalable systems.

Develop and maintain Tailscale's Windows client and contribute to cross-platform client and backend code. Build UI and platform integrations using WinUI/Windows native frameworks, write unit and integration tests, implement Windows platform features while preserving compatibility, and collaborate asynchronously across a distributed engineering team.

Lead resolution of high-severity post-sales escalations: investigate and reproduce complex networking and software issues, run customer calls, collect logs and evidence, create engineering-ready handoff packages, identify systemic patterns, and improve tooling and runbooks to raise Support's technical capability.

Partner with Account Executives to drive new commercial business by leading technical discovery, architecture design, demos and POCs. Guide complex deals, build scalable enablement and provide product/market feedback. Blend deep networking and security expertise with sales acumen to support quota attainment.

Lead the dataplane product vision and roadmap for Tailscale, owning connectivity features (WireGuard, relays, subnet routing, exit nodes, connectors), performance/reliability SLOs, regional relay capacity, operator tooling (console/CLI), and enterprise/regulatory deployments. Partner with engineering, GTM, and customers to drive production traffic commitments and improve connectivity across diverse NATs, OSes, carriers, and networks.