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Frequently asked questions

  • What AI roles is Tailscale hiring for?

    Tailscale currently has 2 active AI-related roles in our index. The most common open titles are: Engineering Manager, Strategic Projects (2). Most positions are in Engineering.

  • What stage of AI development does Tailscale focus on?

    Tailscale's active AI hiring is concentrated in: agents (100%). These categories follow a seven-stage AI lifecycle: data, pre-training, post-training, serving infrastructure, agents, evaluation, and application.

  • What skills does Tailscale look for in AI roles?

    Job postings at Tailscale most frequently mention: Testing Practices, System Design, Open Source Contribution, Market & Technology Trend Analysis, Machine Learning.

  • How many AI roles has Tailscale posted recently?

    In the past 30 days, Tailscale has posted 0 new AI-related roles.

Jobs (78)

2 AI · 39 total active
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Active onlyAI only (≥ 7)
Stage
AllAgent · 6
Function
AllEngineering · 44Product · 28
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AllUnited States · 3Canada · 2
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TitleStageFunctionLocationFirst seenAI score
Software Engineer, Strategic Projects
Software Engineer on a Strategic Projects team focused on demonstrating Tailscale's value for AI infrastructure and agentic tooling. The role involves building prototypes, working with customers on integrations, and creating external artifacts. The team heavily utilizes AI and coding agents, with a strong emphasis on code quality, security, and rapid iteration. Requires Go experience and comfort with AI tools in the engineering workflow.
AgentEngineeringRemote4w ago7
Software Engineer, Strategic Projects
Software Engineer on the Strategic Projects team, focusing on building prototypes and POCs for AI infrastructure and agentic tooling, integrating Tailscale with LLM gateways and customer-facing AI products. The role involves heavy use of coding agents and LLMs, customer integration, and producing external artifacts, with a fast shipping cadence and high bar for code quality and security.
AgentEngineeringRemote4w ago7
Engineering Manager, Strategic Projects
Engineering Manager for a strategic projects team focused on AI-native initiatives, including an identity-aware LLM gateway and heavy use of coding agents. The role involves mentoring senior engineers, partnering with leadership and customers to build and ship prototypes and reference architectures, and setting standards for AI tool usage in development.
AgentEngineeringRemote5w ago7
Engineering Manager, Strategic Projects
Engineering Manager for a strategic projects team focused on AI-native initiatives, including an identity-aware LLM gateway and heavy use of coding agents. The role involves managing senior engineers, partnering with leadership and customers to develop prototypes and reference architectures, and setting standards for AI tool usage in development.
AgentEngineeringRemote5w ago7
Developer Relations Engineer
Developer Relations Engineer at Tailscale, focusing on improving the developer experience for their core VPN/connectivity product and expanding into new areas like secure AI access. The role involves building demos, sample apps, technical content, representing the company at events, and working cross-functionally. Requires strong software engineering background, excellent communication skills, and a deep curiosity about systems, including local AI models.
—EngineeringRemote6w ago5
Senior Product Designer
Senior Product Designer for Tailscale, focusing on the user experience for IT administrators and DevOps engineers managing networks. The role involves discovery, design, and delivery across GUI and CLI, with an emphasis on understanding technical subject matter and collaborating closely with engineers and PMs. The designer will use AI tools to enhance their workflow and explore AI-assisted experiences within technical products.
—ProductRemote7w ago5
Senior Product Designer
Senior Product Designer for Tailscale, a company building secure network interconnection software. The role focuses on designing the user experience for IT administrators, DevOps engineers, and security professionals who manage their networks. The designer will own discovery and design from problem framing to delivery, working across GUI and CLI surfaces. They should be comfortable with technical subject matter, curious about how things work, and able to work independently in a fast-paced, distributed environment. Experience with technically sophisticated B2B or infrastructure products is required. The role will leverage AI tools in the design workflow.
—ProductRemote7w ago5
Staff Product Designer
Staff Product Designer at Tailscale, focusing on the Network Features team. This role involves defining design strategy for complex networking and security products, translating technical systems into user-friendly designs, and leading discovery for ambiguous problems. The designer will partner closely with engineering and PMs, deliver end-to-end design solutions, and explore future-looking design questions. A key aspect is integrating AI tools into the design workflow and developing a point of view on AI-assisted experiences in technical products. Requires 10+ years of experience, a strong portfolio in B2B/infrastructure products, and genuine interest in networking and security.
—ProductRemote7w ago5
Solutions Engineer - Commercial (Expansion Sales)
This role is for a Commercial Solutions Engineer at Tailscale, a company focused on secure network interconnection. The Solutions Engineer will partner with Sales to drive new business, lead technical discovery and architecture design, and act as a trusted advisor to customers. The role requires strong networking and security expertise, sales acumen, and experience with infrastructure as code and cloud platforms. A key responsibility includes understanding AI gateway and governance platforms for LLM access and audit, and familiarity with PAM solutions.
—ProductRemoteJan 95
Software Engineer, Product Strategy
Software Engineer on the Product Strategy team, focusing on building prototypes and POCs for AI agents and tooling, integrating Tailscale for AI use cases, and working with customers on solutions. Requires Go experience and comfort building tools on top of LLMs.
AgentEngineeringRemoteNov '255
Software Engineer, Product Strategy
Software Engineer on the Product Strategy team, focusing on building prototypes and POCs for AI agents/tooling, integrating Tailscale with customers for AI workloads, and creating reference architectures. Requires Go experience and comfort building tools on top of LLMs.
AgentEngineeringRemoteNov '255
Solutions Engineer - Commercial (New Business)
Solutions Engineer for Tailscale, a company building secure network interconnectivity software. This role partners with Sales to drive new business for Commercial customers, focusing on technical discovery, architecture design, and acting as a trusted advisor. The role requires deep networking and security expertise, with an understanding of AI gateway and governance platforms for LLM access and audit.
—ProductRemoteJul '245
Solutions Engineer - Commercial (New Business)
Solutions Engineer for Tailscale, a company building secure network interconnectivity software. This role partners with Sales to drive new business for Commercial customers, focusing on technical discovery, architecture design, and acting as a trusted advisor. It requires deep networking and security expertise, with a specific mention of understanding AI gateway and governance platforms for LLM access.
—EngineeringRemoteNov '235
Backend Engineer, Identity
Backend Engineer focused on identity and access management features for Tailscale, a secure networking product. Responsibilities include developing core software components, identity services, sign-on functionality (SSO, OAuth2, SAML, WebAuthn), SCIM capabilities, and ensuring service observability, security, scalability, and resilience. Requires participation in on-call rotation and a security-first mindset.
—EngineeringRemote1w ago0
Backend Engineer, Identity
Backend Engineer focused on identity and access management features for Tailscale, a secure interconnection product. Responsibilities include developing core software components, identity services, sign-on functionality (SSO, OAuth2, SAML, WebAuthn), SCIM capabilities, and ensuring service observability, security, and stability. Requires participation in on-call rotation.
—EngineeringRemote1w ago0
Frontend Engineer
Frontend Engineer at Tailscale, a company building secure interconnectivity software. The role focuses on owning the technical direction and architecture of the next-generation web console, building frontend infrastructure, and focusing on identity-adjacent systems. This involves defining frontend architecture, designing authentication and session infrastructure, building a serving platform, establishing conventions, creating patterns and tooling, partnering with design, collaborating with other teams, defining testing strategy, improving local development workflows, and raising the quality bar for frontend engineering. The role requires experience with React, web platform fundamentals, and building internal platforms. Nice-to-haves include experience with AI-assisted development tooling, design systems, and identity/B2B SaaS products.
—EngineeringRemote1w ago0
Frontend Engineer
Frontend Engineer role focused on building the next-generation web console for Tailscale, emphasizing identity-adjacent systems, authentication, and cross-origin integrations. The role involves owning technical direction, building frontend infrastructure, and enabling multiple products within a unified console experience. It requires a strong understanding of web platform fundamentals, browser security, and experience building internal platforms.
—EngineeringRemote1w ago0
Software Engineer, Networking (Features)
Software Engineer focused on networking features and optimizations for the Tailscale product, involving backend services, product ideation, and ensuring security and stability of distributed systems. Requires strong Go, distributed systems, and OS-level networking knowledge.
—EngineeringRemote2w ago0
Software Engineer, Networking (Features)
Software Engineer focused on developing and optimizing core networking features and backend services for the Tailscale product, with an emphasis on product lifecycle ownership, system design, and security.
—EngineeringRemote2w ago0
Solutions Engineer (Singapore) - Commercial
Solutions Engineer for Tailscale in APAC, focusing on commercial expansion. Responsibilities include partnering with sales, leading technical engagements, conducting workshops and POCs, and contributing to product development by writing code and developing integrations for strategic customers. The role also involves gathering field insights to inform product and GTM strategies and building reusable technical assets.
—EngineeringRemote3w ago0
Software Engineer, Networking (Edge)
Software Engineer focused on designing, building, and maintaining Tailscale's global networking infrastructure, including Funnel and DERP relay services. Responsibilities involve ensuring scalability, high availability, performance, and security, as well as providing architectural guidance and troubleshooting customer networking issues. The role also contributes to open-source client code and the product's network dataplane.
—EngineeringRemote3w ago0
Software Engineer, Networking (Edge)
Software Engineer role focused on designing, building, and maintaining Tailscale's global Funnel and DERP relay infrastructure, emphasizing network engineering, SRE/DevOps, and customer support for connectivity issues. The role involves contributing to open-source client code and the product dataplane, with a strong focus on security and performance.
—EngineeringRemote3w ago0
Software Engineer, Networking (Dataplane)
Software Engineer role focused on the core client connectivity features of Tailscale, involving network engineering, software development, and ensuring scalability, performance, and security of networking modules. Requires expertise in networking protocols, Go or similar languages, and distributed systems.
—EngineeringRemote3w ago0
Software Engineer, Networking (Dataplane)
Software Engineer role focused on the core client connectivity features of Tailscale, involving network engineering, software development, and ensuring scalability, performance, and security of networking modules. Requires expertise in networking protocols, Go or similar languages, and distributed systems.
—EngineeringRemote3w ago0
Business Operations & Strategy Manager
This role is for a Business Operations & Strategy Manager at Tailscale, focusing on cross-functional projects that drive the company's long-term success. Responsibilities include commercial strategy, international expansion, improving business systems, and pricing architecture. The role also involves driving AI adoption initiatives and performing data analysis. While AI is mentioned as an area of focus for adoption and assistance, the core of the role is business operations and strategy, not direct AI/ML development.
—ProductRemote5w ago0
Business Operations & Strategy Manager
This role is for a Business Operations & Strategy Manager at Tailscale, a company focused on secure device interconnection. The role involves diagnosing and implementing solutions for significant cross-functional problems, including commercial strategy, international expansion, business systems improvement, and pricing architecture. While the role is not directly building AI, it will drive cross-company AI adoption initiatives and perform data analysis to identify opportunities and mitigate challenges. Experience with AI-assisted workflows is a plus.
—ProductRemote5w ago0
Mid-Market Account Executive
Mid-Market Account Executive responsible for expanding and renewing current customer accounts, as well as acquiring net-new customer accounts through inbound leads and outbound prospecting. This role involves owning deals end-to-end, collaborating with various internal teams, and driving revenue growth for Tailscale's products.
—ProductDenver, CO · Hybrid5w ago0
Team Lead, Customer Support
This role is for a Team Lead, Customer Support in Singapore to establish and lead APAC support operations. The role involves managing a team of 8-10 Support Engineers, ensuring world-class service, and providing follow-the-sun coverage. It requires a technical expert passionate about networking problems and mentoring.
—EngineeringRemote6w ago0
Web Strategy & Growth Manager
This role focuses on optimizing the marketing website's digital experience through strategy and experimentation. The manager will lead web initiatives, partner with various teams, and own an experimentation program to improve user engagement and sign-ups. Key responsibilities include web strategy, site ownership, experimentation, and cross-functional collaboration. The ideal candidate has 5+ years of experience in web strategy, growth marketing, or optimization, with hands-on experience in A/B testing and analytics tools.
—ProductRemote6w ago0
Web Strategy & Growth Manager
This role focuses on optimizing the marketing website's digital experience through web strategy, user experience, conversion optimization, and experimentation. The manager will lead strategic web initiatives, partner with various teams, and own a high-velocity experimentation program to improve user engagement and increase sign-ups.
—ProductRemote6w ago0
Staff Product Designer
Staff Product Designer for Tailscale, focusing on network features. This role involves defining design strategy, leading discovery for complex and ambiguous problems, translating technical systems into clear problem frames, and delivering end-to-end design solutions for B2B/infrastructure products. The designer will partner closely with engineering and PMs, influence product direction, and raise the bar for design craft. A key aspect is integrating AI tools into the design workflow and exploring their application in technically complex products.
—ProductRemote7w ago0
Mobile Platform Developer
Software Engineer to join the Tailscale engineering team, focusing on developing the Tailscale product, contributing to client code (Swift, Kotlin, Go) and backend services, with a special emphasis on mobile platforms (iOS and Android).
—EngineeringRemote8w ago0
Mobile Platform Developer
Software Engineer to join the engineering team to develop the Tailscale product, contributing to client code and backend services. The client code is a mix of modern Swift, Kotlin and Go. Prior Go expertise is not a requirement. Bring a special focus on our mobile platforms, iOS and Android, while contributing to common code that supports macOS, Windows and other core client platforms.
—EngineeringRemote8w ago0
Infrastructure Engineer
Software Engineer to join Tailscale's growing team, focusing on shared engineering services and functionalities to support internal business units. The role involves building tools, processes, and owning projects end-to-end, with responsibilities including designing, building, testing, and documenting core software components, ensuring observability, participating in incident response, and improving system efficiency, scalability, and stability.
—EngineeringRemoteApr 200
Brand Designer
Tailscale is seeking a Brand Designer with strong web and UX sensibilities to shape its digital experiences. The role involves designing landing pages, campaign surfaces, and web experiences, balancing brand expression with usability and conversion. Responsibilities include translating brand into scalable web systems, managing projects, supporting experimentation, and collaborating cross-functionally with web, growth, and content teams. The ideal candidate will have 3-6+ years of experience in brand, marketing, or web design, proficiency in design tools like Figma and Adobe Creative Suite, and a strong understanding of UX principles, accessibility, and inclusive design.
—ProductRemoteApr 160
Technical Writer
Tailscale is seeking a Technical Writer to create and deliver high-quality product documentation, tutorials, and guides for networking and security professionals and software engineers. The role involves collaborating with subject-matter experts, product managers, and the community to ensure accurate and accessible content, with a focus on docs-as-code workflows and improving information architecture. Experience with networking, security concepts, Git, and Markdown is required.
—EngineeringRemoteApr 100
Manager, Customer Experience Operations
Manager, Customer Experience Operations for a B2B SaaS company. This role focuses on operationalizing post-sales processes, including customer health scoring, renewal forecasting, and tooling management. While the role mentions leveraging AI for efficiency and familiarity with AI-driven tooling, the core responsibilities are in operations, data analysis, and program management within the customer success and revenue operations functions, not in building or researching AI models.
—ProductRemoteApr 60
Manager, Customer Experience Operations
Manager, Customer Experience Operations for a B2B SaaS company. This role focuses on operationalizing post-sales processes, including customer health scoring, renewal forecasting, and tooling management. While the role mentions leveraging AI for efficiency and familiarity with AI-driven tooling, the core responsibilities are in operations, data analysis, and program management within the customer success and revenue operations functions, not in building or researching AI models.
—ProductRemoteApr 60
Procurement Manager
Tailscale is seeking a Procurement Manager to build and own their procurement function, focusing on software, SaaS, cloud, data, and professional services. The role involves managing the end-to-end procurement process, including intake, sourcing, negotiation, contracting, and renewal management, while partnering with Legal, Security, and Finance. The ideal candidate will have experience building procurement processes from scratch in a high-growth technology environment.
—ProductRemoteMar 200
Procurement Manager
Seeking a Procurement Manager to build and own Tailscale's procurement function, reporting to the VP of Finance. This role involves creating scalable processes for acquiring software and services, managing requests end-to-end (intake, sourcing, negotiation, contracting, renewal), and partnering with Legal, Security, Finance, and internal buyers. The ideal candidate will have strong judgment, ownership, and experience building procurement systems from scratch in a high-growth technology environment.
—ProductRemoteMar 200
Senior Customer Account Executive
Senior Customer Account Executive responsible for expanding and renewing current customer accounts by identifying additional use cases, educating clients on new features, and ensuring successful adoption of Tailscale. This role involves building a pipeline, owning upsell and renewal targets, and collaborating with Solutions Engineering, Customer Success, Support, Marketing, and Product teams. Requires 2+ years of closing experience in an AE or AM role, experience with developer/technical products, and a track record of meeting quota.
—ProductDenver, CO · HybridMar 170
Manager, Sales Development Representative
Manager to lead the Sales Development team, responsible for building qualified pipeline for the sales organization. This role involves coaching and developing SDRs, refining prospecting strategies, and partnering with Sales, Marketing, and Operations.
—ProductToronto, ON +1 · HybridMar 170
Go Core Client Engineer
This role is for a Go Core Client Engineer responsible for designing, implementing, and operating the Go-based shared client code that powers Tailscale's product. The engineer will work on core client subsystems like connection management, NAT traversal, and encrypted transport, shipping end-to-end features and improving reliability, performance, and observability.
—EngineeringRemoteMar 60
Go Core Client Engineer
This role is for a Go Core Client Engineer responsible for designing, implementing, and operating the Go-based shared client code that powers Tailscale's product. The engineer will work on core client subsystems like connection management, NAT traversal, and encrypted transport, focusing on shipping end-to-end features and improving reliability, performance, and observability.
—EngineeringRemoteMar 60
Implementation Engineer
This role focuses on the technical onboarding of customers to Tailscale, ensuring they achieve value quickly. It involves guiding customers through configurations, integrating with identity providers, defining policies, and acting as a feedback loop to product and engineering teams. The role requires strong networking fundamentals and a customer-facing technical background.
—EngineeringRemoteFeb 230
Implementation Engineer
Tailscale is seeking an Implementation Engineer to manage the technical onboarding journey for customers, ensuring they achieve value with the product within 30 days. This role involves guiding customers through configurations like IdP integration and ACL policy definition, acting as a feedback loop to Product and Engineering, and maintaining data hygiene in sales and CSP tooling. The ideal candidate has 2-4+ years of experience in a customer-facing technical role, strong networking fundamentals, and proficiency in software installation and troubleshooting.
—EngineeringRemoteFeb 230
Software Engineer, Engineering Tooling
Software Engineer to join the engineering tooling team, focusing on building and improving shared engineering services, developer tooling, CI/CD, and observability to support internal business units and increase engineering productivity. The role involves end-to-end project ownership, stakeholder collaboration, and incident response.
—EngineeringRemoteFeb 130
Software Engineer, Engineering Tooling
Software Engineer to join the engineering tooling team, supporting internal business units with shared services and functionalities. The role involves building and improving developer tools, CI/CD, and leveraging production data for issue surfacing and business decisions. Responsibilities include designing, building, testing, and documenting software components, ensuring observability, participating in incident response, and analyzing system efficiency.
—EngineeringRemoteFeb 130
Software Engineer, Engineering Tooling
Software Engineer to join the engineering tooling team, focusing on building and improving shared engineering services and functionalities for internal business units. This role involves understanding stakeholder needs, owning projects end-to-end, and enhancing developer productivity through tooling, CI/CD, and observability.
—EngineeringRemoteFeb 130
Content Marketing Specialist
Content Marketing Specialist role focused on creating content for a technical audience in the networking and security space. The role involves collaborating with various teams to translate product positioning into effective content, understanding users, and positioning the company as a thought leader. Experience with B2B/enterprise technology, networking/security products, and SEO is required.
—ProductRemoteFeb 20
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