Jobs at Tailscale

Manage and grow existing customer accounts through upsells and renewals. Build pipeline, create success plans, forecast accurately, educate customers on product value, and collaborate with Sales Engineering, Customer Success, Support, Marketing, and Product. Participate in recorded customer meetings for coaching and quality improvement.

Own the full sales cycle for new business: prospect, qualify inbound leads, self-source one-third of pipeline, close deals with senior technical buyers, run experiments to refine playbooks, represent Tailscale at events, support customers across time zones, and manage pipeline and forecasts in Gong and Salesforce.

Develop and maintain Tailscale’s control plane, relay infrastructure, identity integrations, open-source client code, and backend services. Design, test, document, and operate scalable software with strong observability and security. Participate in incident response and customer escalations, improve system efficiency and stability, and collaborate asynchronously with engineers, designers, and product managers throughout the product lifecycle.

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.

Own and negotiate commercial agreements across customers, vendors, partners, marketplaces, technology, data protection, and confidentiality matters. Advise Sales and go-to-market teams on deal structure, risk, and contracting strategy. Build scalable templates, playbooks, approval processes, and self-service resources. Partner with Security, Privacy, Product, Engineering, Finance, and Operations on technology transactions, global matters, revenue considerations, and risk management. Improve contracting efficiency and support broader legal priorities.

Own and continuously improve onboarding and ongoing enablement programs for revenue team hires. Design scalable role-specific learning paths, manage program logistics and LMS content, partner with sales leaders and cross-functional stakeholders, track ramp and competency metrics, and iterate based on data and feedback. Pilot AI-driven learning tools while supporting skill development, product launches, process rollouts, certifications, and career progression in a remote-first environment.

Build and maintain production-grade dbt data models and pipelines across ingestion, transformation, and visualization. Develop reliable datasets supporting reporting, analysis, finance, revenue recognition, and company decision-making. Collaborate with Finance, Engineering, Sales, Product, and Marketing to understand data needs, improve manual workflows, validate data accuracy, and create scalable solutions using modern data tools.

Lead Tailscale’s Developer Relations Engineering team while remaining hands-on with integrations, prototypes, demos, open-source projects, workshops, tutorials, and technical content. Own the team roadmap, coach technical contributors, collaborate cross-functionally on launches and product feedback, and measure developer engagement, activation, adoption, and business impact. The role requires strong software engineering, developer advocacy, program management, communication, and experience working in public developer ecosystems.

Design, build, and operate Tailscale’s global Funnel and DERP networking infrastructure. Develop open-source client dataplane features, improve scalability and reliability, troubleshoot complex connectivity issues, support customer escalations, and participate in incident management. The role requires strong networking expertise across VPNs, NAT traversal, routing, and IP addressing, plus experience with distributed systems, SRE, DevOps, and preferably Go.

Design, build, test, document, and optimize Tailscale’s client-side networking software. Develop connectivity features involving routing, VPNs, subnet routers, exit nodes, and NAT traversal; apply secure, scalable architectures; diagnose complex customer network issues; support escalations; collaborate across product and engineering teams; and contribute to open-source networking projects.

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.

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.

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.