Tailscale

Full-stack Engineer

• Develop the Tailscale product, contributing to open-source client code and related backend services, with emphasis on networking features and optimizations
• Take ownership of the entire product lifecycle, from writing code to product ideation and strategic decision-making
• Work with UX/UI designers and product managers to shape networking features
• Design, build, test, and document core networking software components
• Build observability into running services, participate in incident response, and handle customer support escalations
• Analyze and improve the efficiency, scalability, and stability of networking systems and resources
• Apply a security-first mindset to the design and implementation of networking components

Software Engineer – Networking, Features

• Develop the Tailscale product, contributing to open-source client code and related backend services, with emphasis on networking features and optimizations
• Take ownership of the entire product lifecycle, from writing code to product ideation and strategic decision-making
• Work with UX/UI designers and product managers to shape networking capabilities
• Design, build, test, and document core networking software components
• Build observability into running services, participate in incident response, and handle customer support escalations
• Analyze and improve the efficiency, scalability, and stability of networking systems and resources
• Apply a security-first mindset to networking design and implementation

Software Engineer, Networking – Features

Account Executive

• Own and grow a territory of enterprise organizations, driving net-new customer acquisition and expansion opportunities
• Self-source pipeline through outbound prospecting, cold outreach, strategic account targeting, and networking
• Own the full sales cycle from lead to close
• Develop strategic account plans covering stakeholders, organizational priorities, technical initiatives, and expansion paths
• Build relationships with Security, Infrastructure, Engineering, Compliance, and Executive stakeholders
• Navigate complex enterprise sales cycles involving multiple decision-makers, procurement, security reviews, and legal negotiations
• Position Tailscale as a strategic platform for secure connectivity and modern network access
• Lead cross-functional account teams across Sales Engineering, Customer Success, Product, Marketing, and Support
• Drive adoption beyond initial deployment through broader organizational usage and long-term account growth
• Exceed quota through self-generated pipeline, new customer acquisition, and account expansion
• Establish trusted advisor relationships with technical and business leaders
• Drive adoption from initial deployment to broader organizational standardization
• Build predictable pipeline through disciplined prospecting and strategic account development

Enterprise Account Executive

• Own and grow a territory of enterprise organizations through net-new customer acquisition and expansion opportunities
• Self-source pipeline through outbound prospecting, cold outreach, strategic account targeting, and networking
• Own the full sales cycle from lead to close
• Develop strategic account plans identifying stakeholders, priorities, technical initiatives, and expansion paths
• Build relationships with Security, Infrastructure, Engineering, Compliance, and Executive stakeholders
• Navigate complex enterprise sales cycles involving decision-makers, procurement, security reviews, and legal negotiations
• Position Tailscale as a strategic platform for secure connectivity and modern network access
• Lead cross-functional account teams across Sales Engineering, Customer Success, Product, Marketing, and Support
• Drive adoption beyond initial deployment and identify long-term account growth opportunities
• Exceed quota through self-generated pipeline, new customer acquisition, and account expansion
• Establish trusted-advisor relationships with technical and business leaders
• Drive adoption from initial deployment to broader organizational standardization
• Build predictable pipeline through prospecting and strategic account development

Backend Engineer

• Develop the Tailscale product, contributing to open source client code and related backend services
• Own the entire product lifecycle, from writing code to product ideation and strategic decision-making
• Work with UX/UI designers and product managers to shape features
• Design, build, test, and document core software components
• Develop features across the control plane, relay infrastructure, and identity integrations
• Build observability into running services, participate in incident response, and handle customer support escalations
• Analyze and improve system efficiency, scalability, and stability
• Apply a security-first mindset to design and implementation

Backend Engineer, Control Plane

General Counsel

• Lead day-to-day commercial legal support as Tailscale grows
• Own and negotiate enterprise customer, vendor, partner, marketplace, technology, data protection, and confidentiality agreements
• Advise Sales and go-to-market teams on deal structure, contracting strategy, risk, and escalation paths
• Translate legal issues into clear options and recommendations for timely decisions
• Build and improve templates, playbooks, fallback positions, approval thresholds, intake processes, and self-service resources
• Partner with Security, Privacy, Product, and Engineering on customer commitments involving data, security, product functionality, integrations, artificial intelligence, and emerging technologies
• Work with Finance and Revenue Operations on pricing terms, revenue considerations, procurement, insurance, and other commercial matters
• Support international transactions and coordinate with outside counsel when local or specialized expertise is needed
• Identify negotiation patterns and use data to improve cycle time, consistency, and customer and internal team experience
• Contribute to other legal priorities as the company and legal function evolve
• Report to the Head of Legal

Commercial Legal Counsel

• Build and evolve the strategy, priorities, operating model, and team for Tailscale’s legal function
• Advise executives and cross-functional leaders on legal and business considerations
• Help leaders identify material risks, evaluate tradeoffs, and apply appropriate safeguards
• Partner with Product, Engineering, Security, Sales, Finance, People, Operations, Marketing, and other teams
• Advise on corporate governance, product development, open-source software, intellectual property, privacy, data, AI, security, employment, commercial relationships, compliance, and international operations
• Build scalable legal processes, policies, systems, and decision-making frameworks
• Determine which legal capabilities should be developed internally, delegated to team members, or supported by outside counsel
• Hire and empower legal team members, including building a dedicated commercial legal capability
• Select and manage outside counsel across the countries where Tailscale operates
• Coordinate guidance across jurisdictions and translate local requirements into consistent company practices
• Support strategic partnerships, corporate initiatives, and other business-critical matters
• Anticipate emerging legal and regulatory developments and help the company prepare
• Shape how Legal operates at Tailscale as the company grows

Head of Legal

• Lead day-to-day commercial legal support as Tailscale grows
• Own and negotiate enterprise customer, vendor, partner, marketplace, technology, data protection, and confidentiality agreements
• Advise Sales and go-to-market teams on deal structure, contracting strategy, risk, and escalation paths
• Translate legal issues into clear options and recommendations for timely decisions
• Build and improve templates, playbooks, fallback positions, approval thresholds, intake processes, and self-service resources
• Partner with Security, Privacy, Product, and Engineering on customer commitments involving data, security, product functionality, integrations, artificial intelligence, and emerging technologies
• Work with Finance and Revenue Operations on pricing terms, revenue considerations, procurement, insurance, and other commercial matters
• Support international transactions and coordinate with outside counsel when local or specialized expertise is needed
• Identify negotiation patterns and use data to improve cycle time, consistency, and customer and internal-team experience
• Contribute to other legal priorities as the company and legal function evolve
• Report to the Head of Legal

• Build and evolve the strategy, priorities, operating model, and team for Tailscale’s legal function
• Advise executives and cross-functional leaders on legal and business matters
• Help leaders identify material risks, evaluate tradeoffs, and implement appropriate safeguards
• Partner with Product, Engineering, Security, Sales, Finance, People, Operations, Marketing, and other teams
• Advise on corporate governance, product development, open-source software, intellectual property, privacy, data, AI, security, employment, commercial relationships, compliance, and international operations
• Build scalable legal processes, policies, systems, and decision-making frameworks
• Determine which legal capabilities should be developed internally, delegated to future team members, or supported by outside counsel
• Hire and empower legal team members, including building a dedicated commercial legal capability
• Select and manage outside counsel across countries where Tailscale operates
• Coordinate guidance across jurisdictions and translate local requirements into practical company practices
• Support strategic partnerships, corporate initiatives, and business-critical matters
• Anticipate emerging legal and regulatory developments and help the company prepare

Onboarding Specialist

• Own and continuously improve onboarding for new revenue hires, from pre-boarding through ramp milestones
• Extend onboarding into continuous everboarding enablement so reps keep building skills after initial ramp
• Design, launch, and manage recurring enablement programs covering skill development, product launches, process rollouts, and certifications
• Build scalable, role-specific enablement paths supporting core competencies and career progression
• Manage program logistics, content, cadence, schedule, and quality end to end
• Partner with frontline managers and sales leadership to identify skill gaps and deliver targeted programs
• Instrument programs with ramp-time, completion, and competency metrics and iterate based on data and rep feedback
• Manage the Tailscale LMS and keep new-hire materials current and accessible
• Explore and pilot AI-driven learning tools such as an AI tutor for asynchronous onboarding
• Collaborate across Sales, Customer Engineering, Support, Customer Success, Marketing, and Product

Enablement Program Specialist – Onboarding

• Own and continuously improve onboarding for new revenue hires, from pre-boarding through ramp milestones
• Extend onboarding into continuous everboarding enablement so representatives keep building skills after initial ramp
• Design, launch, and manage recurring enablement programs covering skill development, product launches, process rollouts, and certifications
• Build scalable, role-specific enablement paths supporting core competencies and career progression
• Manage program logistics, content, and cadence end to end while maintaining schedule and quality
• Partner with frontline managers and sales leadership to identify skill gaps and deliver targeted programs
• Instrument programs with ramp-time, completion, and competency metrics and iterate based on data and representative feedback
• Manage the Tailscale LMS to keep new-hire materials current and accessible
• Explore and pilot AI-driven learning tools, such as an AI tutor for asynchronous onboarding
• Collaborate across Sales, Customer Engineering, Support, Customer Success, Marketing, and Product