Jobs at Tailscale

Leads and develops Talent Acquisition Partners, sets recruiting strategy, monitors hiring performance, and advises senior business leaders on talent priorities. The role oversees recruiting across technical and business functions, supports complex searches, uses pipeline and market data to improve outcomes, and partners with Sourcing and Talent Acquisition Operations on processes, systems, analytics, and scalable recruiting programs.

Lead advanced sourcing strategies for complex technical, leadership, GTM, and specialized searches. Identify and engage passive talent through research, market mapping, technical communities, and creative channels. Use sourcing data and market intelligence to guide hiring strategies, champion inclusive sourcing, cultivate candidate relationships, and ensure effective handoffs. Share sourcing expertise, build reusable talent resources, and improve tools, workflows, analytics, automation, and AI-enabled practices across Talent Acquisition.

Lead full-cycle recruiting for high-priority go-to-market roles, especially Sales, across global markets. Advise GTM leaders on hiring strategy, talent availability, market intelligence, workforce planning, interview processes, and recruiting data. Build pipelines, assess and close candidates, manage multiple searches, improve recruiting processes, and partner with Talent Acquisition, Revenue Operations, Finance, and sourcing teams to scale commercial hiring in a high-growth SaaS environment.

Own and scale Talent Acquisition operations, including recruiting systems, analytics, reporting, process improvement, coordinator workflows, automation, compliance, and cross-functional operational programs. Administer recruiting technologies, build dashboards, improve data quality, support hiring forecasts, and develop scalable documentation and processes. Partner with TA leadership and teams across People, Finance, IT, Legal, and the business to improve recruiting effectiveness and candidate experience.

Manage end-to-end sales compensation operations including monthly commission processing, audits, and CaptivateIQ administration. Partner with Revenue Leadership, Finance, and Payroll on compensation design, quota modeling, and incentive strategy. Deliver analytics and reporting on attainment, payouts, and quota performance while improving systems, automations, integrations, and operational governance.

Partner with Account Executives to drive new commercial deals by leading technical discovery, solution architecture, demos, and POCs. Serve as trusted advisor across stakeholders, co-own pipeline and quota outcomes, produce enablement assets, and provide product and GTM feedback. Focus on networking, zero-trust, IAM, PAM, and cloud architecture.

Build and maintain core billing systems: integrate third-party billing platforms, implement metering/pricing/rating for subscriptions and usage, ensure accurate usage tracking, automate reconciliation and reporting, establish observability and incident response, and collaborate with product, finance, and support teams to deliver reliable billing features.

Drive product positioning, messaging, and go-to-market for Tailscale by collaborating with product, sales, and marketing. Launch features, create sales enablement content, perform competitive analysis, represent PMM at events, and measure pipeline and revenue impact.

Designs and implements security controls across cloud platforms, operating systems, Kubernetes, networks, and CI/CD. Audits infrastructure for vulnerabilities, develops security and privacy improvements, performs threat modeling, and drives remediation. The role includes software development, infrastructure security analysis, and serving as an infrastructure-level subject matter expert during security incidents.

Own brand design projects from concept through delivery across web, campaigns, events, social media, presentations, product marketing, and internal communications. Extend visual identity, build reusable templates and design systems, present concepts, incorporate feedback, and manage multiple priorities. Collaborate with marketing, content, product marketing, web, developers, and other designers to deliver polished, consistent creative assets.

Provide Tier 1 technical support by resolving configuration and networking issues, managing a high-volume ticket queue, meeting response and resolution targets, and maintaining strong customer satisfaction. Troubleshoot across macOS, Windows, Linux, and mobile operating systems, explain technical concepts clearly, and collaborate with Customer Experience, Product, and Engineering teams to identify recurring user issues and improve the customer experience.

Provide Tier 2 technical support and escalations for Tailscale customers, troubleshoot complex networking and SSO issues, manage ticket SLAs, mentor Tier 1, collaborate with Product/Engineering, and drive improvements to user experience while maintaining high CSAT.

Build and maintain internal AI enablement tools, workflows, and guardrails to help engineers use coding agents and LLMs safely. Evaluate models, partner with teams to apply AI, track adoption and impact, and provide documentation, coaching, and advocacy to increase engineering velocity.

Design and implement security and privacy features across Tailscale's codebase. Audit features for vulnerabilities, perform threat modeling and security analysis, drive mitigations to resolution, and spend significant time writing secure software (50%+ coding). Collaborate with engineering teams to promote secure coding and provide guidance and training.

Create technically accurate, growth-focused educational content (tutorials, guides, demos, comparisons) that helps enterprise and developer audiences discover, evaluate, and adopt Tailscale. Monitor communities and search signals, collaborate with product and engineering, optimize existing content, and build an AI-first program to drive self-serve revenue and product adoption.

Serve as the technical lead for strategic customers: onboard, train, troubleshoot, and drive adoption of Tailscale. Build relationships, conduct QBRs, recommend best practices, escalate product feedback, and maintain customer-facing documentation to enable long-term success and expansion.

Build and maintain internal engineering services and automation to support product teams. Improve observability, CI/CD, infrastructure as code, and cloud-managed services. Own running services, participate in incident response, collaborate cross-functionally, and drive reliability, scalability, and efficiency improvements.

Lead frontend architecture and platform work for a unified web console: design app structure, cross-origin auth and session infrastructure, shared UI/platform abstractions, testing strategy, developer workflows, and tooling. Collaborate with product, design, growth, and infrastructure teams, provide technical leadership, mentor engineers, and participate in on-call rotation.

Drive technical success with channel partners by leading discovery, architecture, demos, and POCs for partner-sourced and co-sell deals. Enable partners via training, blueprints, and scalable assets, advise on zero-trust, identity integrations, cloud/hybrid deployments, and collaborate cross-functionally to grow partner-sourced revenue.

Build and maintain Tailscale's native Windows client using C#, XAML, and WinUI/Windows App SDK. Implement platform integrations and UI components, ensure compatibility across Windows versions, write unit and integration tests with Microsoft Testing Platform v2 and xUnit, and contribute to cross-platform client and backend code (including Go). Collaborate asynchronously within a distributed team and iterate quickly in a startup environment.