Jobs at Tailscale

Own the vision, strategy, roadmap, and business growth of Tailscale’s Workload Connectivity product. Lead Kubernetes, ephemeral workload, AI agent, and cloud infrastructure connectivity initiatives; define developer experiences, pricing, packaging, success metrics, and integrations. Partner with engineering, design, operations, and go-to-market teams while engaging technical customers and guiding products from strategy through adoption and revenue impact.

Own and grow Tailscale’s analyst relations program by managing analyst inquiries, briefings, evaluations, research participation, and relationships. Synthesize analyst intelligence and market trends into recommendations for Product Marketing, Product, Engineering, and leadership. Develop analyst-facing materials, support market research, track program effectiveness, and strengthen the company’s positioning across cybersecurity, networking, infrastructure, AI, and emerging technology markets.

Own the vision, strategy, and roadmap for Tailscale’s Identity portfolio, including authentication, authorization, SSO, SCIM, access policies, and user management. Lead admin and end-user experiences across the console, API, and clients. Partner with engineering, product, and design, develop customer insights, and translate customer, support, and competitive signals into priorities. Ensure identity services are secure, reliable, intuitive, and integrated across Tailscale’s platform.

Own the vision, strategy, roadmap, and operator experience for Tailscale’s networking features, including App Connectors, DNS, Funnel, and Tailscale Services. Partner with go-to-market, customer success, and solutions engineering teams on strategic customer commitments. Develop customer insights, define product requirements, launch products, and iterate using data. Simplify complex networking systems through effective object models, defaults, configuration experiences, documentation, and error messaging.

Own and improve Tailscale’s software release management process, including release cadence, readiness criteria, rollout coordination, tooling, runbooks, go/no-go decisions, and operational metrics. Partner with engineering, product, TPM, and support teams to identify risks, coordinate planning, maintain release schedules, and drive scalable process improvements. Requires strong technical fluency in software delivery, deployment pipelines, branching, feature flags, and production operations.

Lead and mentor software engineering teams across multiple product pods. Provide technical direction, oversee production services and operational readiness, manage on-call and incident response, support hiring and career development, and drive cross-functional planning and delivery. The role requires strong people-management experience, technical judgment, production-service expertise, and the ability to work asynchronously in a distributed startup environment.

Develop and improve Tailscale’s security and privacy features, identify and resolve technical vulnerabilities, conduct security audits, perform threat modeling, and guide engineering teams on secure coding. The role spends at least half its time writing software and requires knowledge of application security, web vulnerabilities, client-side security, API flaws, cryptography, and networking protocols.

Build and maintain core billing software, including subscription and usage-based pricing, metering, rating, reconciliation, reporting, and third-party billing integrations. Ensure billing data integrity, observability, reliability, and high availability. Collaborate with product, finance, sales, support, and engineering teams on custom billing requirements, lead incident response, contribute to architecture and design reviews, and mentor engineers.

Own and scale Tailscale’s Product operations, including roadmap health, launch readiness, documentation, onboarding, feature request management, customer insight systems, operating rhythms, and product metrics. Partner with Product, GTM, Support, Data, and company leadership to identify operational gaps, establish standards, influence prioritization, and build scalable systems. The role requires autonomous execution, strategic judgment, cross-functional alignment, and strong communication in a remote-first environment.

Build and evolve Tailscale’s customer-facing documentation platform, docs-as-code tooling, content publishing pipelines, API documentation, and search infrastructure. The role includes full-stack development, CI/CD and automated testing, platform scalability, cross-functional collaboration with engineering, product, design, research, and growth teams, and engagement with open-source contributors. The engineer will also research documentation trends and consider how LLMs consume and interact with published content.

Develop and scale integrated account-based marketing campaigns for Enterprise and Mid-Market audiences. Own campaign strategy, audience segmentation, messaging, paid LinkedIn advertising, personalized landing pages, direct mail, gifting, Sales outreach, and performance optimization. Partner with Sales, GTM Operations, Product Marketing, Content, Events, and Partner Marketing to drive account engagement, meetings, pipeline creation, and progression.

Build and lead the frontend architecture for Tailscale’s next-generation web console. Responsibilities include developing shared frontend infrastructure, identity and authentication systems, cross-origin session management, testing strategies, developer tooling, deployment workflows, and unified product experiences. The role partners across design, growth, product, infrastructure, and engineering while providing technical leadership, mentoring, and on-call incident support.

Leads technology integration partnerships from opportunity identification through technical discovery, solution design, commercial alignment, launch, and adoption. Works with technology partners, customers, Product, Engineering, Sales, Legal, Finance, Marketing, and Customer Success. Evaluates APIs, authentication, security, architectures, and data flows; develops business cases; negotiates partnership terms; and influences integration priorities. The role focuses on partnerships across networking, security, identity, infrastructure, AI, and developer tools.

Design growth-focused product experiences that improve activation, onboarding, monetization, expansion, and referrals. Develop experiment ideas, prototypes, and minimum-viable solutions; collaborate with product managers, researchers, designers, and engineers; interpret experiment results; and iterate based on user feedback while maintaining a high design-quality bar.

Lead Tailscale’s global communications function, including product, corporate, internal, executive, crisis, international, and media communications. Build market visibility and thought leadership around secure connectivity, networking, cybersecurity, and AI infrastructure. Develop media and journalist relationships, oversee agencies and awards, advise executives, manage high-stakes communications, and hire a high-performing team while establishing scalable processes and performance measurement.

Own strategic enterprise accounts with 10,000+ employees, developing account plans, generating pipeline, managing complex six- and seven-figure SaaS deals, building executive relationships, and driving expansion. Partner cross-functionally with SDRs, Marketing, Engineering, Product, Customer Success, Legal, Finance, and leadership. Maintain accurate forecasts and CRM records while helping establish Tailscale’s enterprise sales playbook.

Own and improve Engineering, Product, and Design operational processes, including bug tracking, incidents, reliability, escalations, planning, reviews, and project tracking. Build Jira and Snowflake dashboards, analyze operational health data, identify trends, and implement process improvements. Partner with technical leadership in a remote startup, coordinate cross-functional initiatives, support retrospectives, and bring structure to ambiguous projects.

Build and operate infrastructure and shared engineering services for internal teams and Tailscale’s product. Responsibilities include improving observability, CI/CD, cloud infrastructure, managed services, Kubernetes, and service automation; designing, testing, and documenting software components; participating in incident response; supporting customer escalations; and improving system efficiency, scalability, and stability.

Partner with Account Executives on enterprise sales cycles by leading technical discovery, architecture, demos, proofs of concept, security reviews, and early adoption. Design secure Tailscale solutions for hybrid, multi-cloud, and on-premises environments, advise networking and security stakeholders, support pipeline and quota outcomes, and provide customer feedback to Product, Engineering, and go-to-market teams. Occasional travel of approximately 10–20% is required.

Leads and builds Tailscale’s global legal function, advising executives and cross-functional teams on corporate governance, product, privacy, data, security, intellectual property, employment, commercial, compliance, and international matters. Establishes legal strategy, processes, systems, and operating models; hires and develops the legal team; manages outside counsel; supports strategic transactions and partnerships; and translates complex legal and regulatory issues into practical business guidance.