Tailscale

Thank you for considering Tailscale . If this job description resonates with you, please apply. Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. We encourage you to help us break that statistic! About Tailscale Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We're building a future for the Internet that's easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital. About the Role We are seeking a strategic, creative, and highly experienced Head of Communications to lead and scale Tailscale's global communications function. This leader will shape how Tailscale is understood by the market, elevate our visibility in the media, and build the communications engine needed to support our next phase of growth. Tailscale is a multi-product secure connectivity platform spanning networking, privileged access, workload connectivity, and AI infrastructure. We have an opportunity to help define the future of secure connectivity, establishing Tailscale as the obvious and best networking choice for AI and agentic infrastructure. We're looking for someone who can turn our technical innovation, customer impact, and vision into compelling stories that earn attention and establish Tailscale as a category leader. Reporting to the SVP of Marketing, you will own product and corporate communications, public relations, media strategy, internal communications, crisis communications, award applications, international comms and media relations, new media engagement, and executive communications across the leadership team outside the CEO. You'll also partner closely with a separate dedicated CEO and policy communications leader to ensure our stories are coordinated and consistent. This is a builder role for someone who combines strong strategic judgment with exceptional execution. You will initially be hands-on while hiring and developing a small, high-performing team. You will work directly with leaders across Product, Engineering, Marketing, People, Legal, and the executive team to build a communications function that can scale with Tailscale's ambitions. Key Responsibilities Develop and execute Tailscale's global communications strategy, strengthening brand awareness, reputation, and market leadership. Lead product and technology communications, translating complex innovations, product launches, and customer stories into compelling narratives that earn meaningful media coverage. This should include sustained product storytelling between launches, including through independent reviews, technical publications, comparisons, creators, and third party validation. It could also include research-led PR. Build strong relationships with top-tier business, technology, cybersecurity, and AI journalists, driving proactive media opportunities and increasing Tailscale's share of voice. Expand Tailscale's presence across emerging media channels, including influential podcasts, newsletters, creators, and technical communities. Own corporate communications for major company milestones, strategic partnerships, funding announcements, and other business developments. Build and scale international communications programs, including regional media relations and agency partnerships. Develop executive communications and thought leadership programs for the leadership team outside the CEO, including speaking opportunities, media engagements, and executive social presence. Partner closely with the dedicated CEO and policy communications lead to coordinate company narratives, major announcements, and executive engagement, building comms campaigns for executives that align with the overall company narrative. Oversee internal communications, partnering with People and executive leadership on company-wide messaging, all-hands, organizational changes, and employee engagement communications. Lead crisis communications, establishing response plans and partnering with Legal, Security, Engineering, and leadership to protect customer trust and company reputation. You should be able to improve processes over time as we scale. Own Tailscale's awards and recognition strategy, identifying and securing high-value industry and company accolades. Hire, manage, and develop a high-performing communications team while overseeing external agencies, communications processes, and performance measurement. This team will start small (likely 2 heads), but has the potential to grow in the future as we scale. Partner closely with the dedicated CEO and policy communications individual contributor to maintain

Thank you for considering Tailscale . If this job description resonates with you, please apply. Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. We encourage you to help us break that statistic! About Tailscale Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We're building a future for the Internet that's easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital. About the Role We are hiring a Commercial Legal Counsel to lead day-to-day commercial legal support as Tailscale continues to grow. You will partner closely with Sales, Partnerships, Finance, Security, Product, and Operations to help the company close business, manage risk, and build contracting practices that scale. This role reports to the Head of Legal. The strongest candidate may be an experienced commercial counsel ready for broader ownership, a senior counsel who has led complex transactions and programs, or a commercial legal leader who can shape the function while remaining hands-on. Key Responsibilities Own and negotiate a broad range of commercial agreements, including enterprise customer, vendor, partner, marketplace, technology, data protection, and confidentiality agreements. Advise Sales and other go-to-market teams on deal structure, contracting strategy, risk, and escalation paths. Translate legal issues into clear options and recommendations that help teams make 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 patterns in negotiations and use data to improve cycle time, consistency, and the experience of customers and internal teams. Contribute to other legal priorities as the company and legal function evolve. What We Are Looking For A law degree and active membership in at least one applicable bar or equivalent authorization to practice law. Meaningful experience advising technology companies on commercial transactions, including in-house experience or equivalent experience working closely with technology clients. Experience helping a legal function, contracting program, or business process scale in a startup or high-growth environment. Strong judgment and the ability to distinguish material business risk from issues that can be addressed through practical guardrails. A record of leading negotiations with sophisticated customers, partners, vendors, or counterparties. Clear, concise communication and the ability to build trust across Legal, Sales, Finance, Security, Product, and executive teams. Comfort working independently, prioritizing competing demands, and making progress with incomplete information. A collaborative approach that creates appropriate ownership and avoids making Legal an unnecessary bottleneck. Nice to Have Commercial work involving developer tools, cloud infrastructure, networking, cybersecurity, software as a service, or open-source products. Experience with enterprise sales, product-led growth, channel or technology partnerships, marketplaces, integrations, or application programming interfaces. Familiarity with privacy, data protection, security, artificial intelligence, intellectual property, or product counseling issues that arise in technology transactions. Experience supporting global customers or coordinating advice across multiple jurisdictions. Experience selecting or implementing contract lifecycle management tools, workflow automation, or commercial legal metrics. Experience mentoring colleagues or helping define the structure and priorities of a growing commercial legal capability. As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale's compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire's base salary. Individual offers may vary based on experience and skill set. CAN Pay Range $250,580—$313,560 CAD What We Offer An inclusive, flexible environment where you can be your authent

Thank you for considering Tailscale . If this job description resonates with you, please apply. Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. We encourage you to help us break that statistic! About Tailscale Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We're building a future for the Internet that's easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital. About the Role We're seeking a talented and motivated full-time Software Engineer, AI Enablement to help Tailscale's engineering organization get the most out of AI-assisted development. You'll join a small, high-leverage team reporting to our co-founder, working alongside our first AI enablement engineer to build the tools, workflows, and practices that help every engineer at Tailscale build faster and more safely with AI. This is a foundational role — you'll have real latitude to shape what AI enablement means here as we scale, with direct visibility into how the whole engineering org adopts these tools. Key Responsibilities Partner with engineering leadership and Tailscale's technical staff to define and drive our internal AI-enablement roadmap. Work closely with the team building Aperture by Tailscale, our AI gateway used both internally and offered as a product. Build and iterate on the tools, workflows, and shared practices that help engineers get real value from coding agents — and evaluate new models and tools, making clear calls on what we adopt. Partner with engineering and non-engineering teams to find high-leverage opportunities to apply AI — this is a support function, so success means other teams shipping faster because of what you've built. Establish the guardrails, review practices, and documentation that make AI-generated code safe to ship, and act as the internal advocate who helps teams adopt good practices without mandating a single tool. Track adoption and measure the real impact of AI tooling on velocity and quality, and report back to leadership. What We Are Looking For 5+ years of professional software engineering experience Genuine, daily, hands-on fluency with modern AI coding tools (Claude Code, Codex, Pi, or similar) — real power-user experience, not occasional use Experience building and shipping internal tools or developer-facing automation Strong written and verbal communication and internal advocacy skills — comfortable teaching, writing, and influencing engineers at very different comfort levels with AI tooling A balanced approach — trying to get people to use AI effectively and safely where appropriate. We don't have an 'AI mandate'; we believe that if we make AI both easy to use and safe, people will choose to use it when appropriate. Comfort with ambiguity and self-directed prioritization on a small, still-forming team Product or systems thinking — able to identify and prioritize high-leverage opportunities, not just execute a pre-set roadmap Nice to Have Prior experience in developer experience, platform engineering, or internal tooling Experience evaluating or benchmarking LLMs and coding agents Experience with a systems language such as Go or Rust, in addition to Python Background in security or code-review practices — helpful for reasoning about AI/agent-generated code, though you don't need to be a security engineer Experience in developer relations, technical evangelism, or customer-facing developer advocacy — the same skills that make someone effective in external DevRel translate well to driving internal AI adoption Technical project management experience As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale's compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire's base salary. Individual offers may vary based on experience and skill set. UK Pay Range £128,770—£178,540 GBP What We Offer An inclusive, flexible environment where you can be your authentic self. We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life. A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles). Comprehensive group benefits with no waiting period. Take advantage of coverage for health, vision, dental, and more for you and your f

About Tailscale Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We're building a future for the Internet that's easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital. About the Role If you're passionate about solving complex technical problems and helping build trust between customers and engineering, this is the role for you. We're seeking a motivated Customer Reliability Engineer to join our team. You'll take ownership of our most complex, ambiguous customer escalations, solving issues where the root cause is not always obvious. You will work these issues to resolution or alternatively a fully-documented handoff that engineering can act on without delay. As a Customer Reliability Engineer, you'll partner closely with the Customer Success Team, Support Team, and Product/Engineering to close the gap between "customer has described a problem" and "engineering has what it needs to fix it." This role reports directly to the Customer Reliability Engineer Team Lead. Key Responsibilities Own high-severity, post-sales technical escalations from intake through resolution or engineering handoff. This includes deep-dive investigations and reproduction of difficult-to-isolate bugs. Get on calls with customers, pull logs, and communicate with the customer about leading theories. Build engineering handoff packages that require minimal follow-up questions: reproducible case, log evidence (timestamps, node IDs), version matrix, impact scope, what's already been ruled out, and a proposed engineering team to own the fix. File and track issues for confirmed bugs, keeping the ticket/issue link intact so engineering retains full customer context. Monitor for patterns across escalations to catch recurring or systemic issues early; translate what you learn into product improvements, tooling, and runbooks that raise the technical bar for the whole Support org. Partner with Support, CSE, and Product/Eng, while staying within this team's scope. What We Are Looking For 4+ years in a technical support or escalation role at a SaaS or infrastructure company, with demonstrated ownership of escalated/enterprise-tier accounts. A genuine problem-solver who gets energy from untangling hard, ambiguous technical issues Comfortable owning a live, high-stakes customer call: staying calm, building trust, and communicating clearly with a frustrated or technical customer under pressure. Hands-on networking experience in production or homelab environments: TCP/IP, routing, DNS, firewalls, NAT, VPNs, load balancers. Deep familiarity with overlay networking concepts — WireGuard, UDP hole punching, STUN — and comparable VPN/networking products. Code-level debugging capability: can read Go source, reason about goroutines/locks/channels, read pprof CPU/heap profiles, and understand network interface semantics. Comfortable with infrastructure concepts: cloud IaaS, CI/CD pipelines, containerized applications, and Kubernetes debugging. Strong systems administration skills as well as troubleshooting across Linux, macOS, and Windows. Track record of independently building reproducible test cases and clear, evidence-backed bug reports engineering can act on directly. Strong technical storytelling: able to distill highly technical, ambiguous issues into clear narratives for both engineers and non-technical stakeholders. Investigative mindset; curious to analyze root cause, and evaluate all options to get customers to the best solution Proficiency with programming/scripting in Go, Python, JSON Experience with packet-level analysis As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale's compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire's base salary. Individual offers may vary based on experience and skill set. US Pay Range $115,000—$144,000 USD Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. We encourage you to help us break that statistic! What We Offer An inclusive, flexible environment where you can be your authentic self. We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life. A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles). Comprehensiv

About Tailscale Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We're building a future for the Internet that's easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital. About the Role Tailscale is looking for an experienced Brand Designer to help bring our brand to life across every customer touchpoint. You'll create thoughtful, high-quality creative that helps people understand our products, builds trust with technical audiences, and supports some of our most important marketing initiatives. This role reports to the Team Lead and partners closely with Brand, Growth, Web, Content, Product Marketing, and Developer Relations. You'll own projects from concept through execution, contribute to the evolution of our design systems, and help us scale creative output without sacrificing quality. We're looking for someone who cares deeply about craft, thrives in collaborative environments but is able to work autonomously while requiring minimal direction, and enjoys solving complex communication problems through thoughtful design. Key Responsibilities Own brand design projects from creative brief through final delivery with limited guidance Design high-quality creative assets across web, campaigns, events, social media, presentations, product marketing, and internal communications Apply and thoughtfully extend Tailscale's visual identity across new formats and channels Create reusable templates, design systems, and creative processes that improve consistency and efficiency Partner closely with Growth, Web, Product Marketing, Content, and Developer Relations to deliver cohesive customer experiences Present design concepts and rationale to stakeholders and thoughtfully incorporate feedback Balance multiple projects while consistently delivering polished, production-ready work Contribute ideas that improve the quality, scalability, and effectiveness of our creative work What We Are Looking For 3+ years of professional experience in brand, marketing, or visual design Strong portfolio demonstrating exceptional design foundations: color theory, accessibility, typography, layout, and storytelling Fluency in Figma and Adobe Creative Cloud Experience designing for digital marketing, websites, campaigns, and brand systems Strong understanding of production-ready design across digital and print Excellent communication and presentation skills Ability to manage multiple projects and priorities with minimal oversight Experience collaborating cross-functionally with marketers, writers, developers, and other designers Strong attention to detail with a high bar for quality and consistency Comfortable giving and receiving constructive design feedback Actively seeks opportunities to refine processes, improve project organization, and make collaboration more effective through thoughtful recommendations. Curious by nature, with a desire to learn about the technical world of networking. Nice to Have Experience designing for B2B SaaS or developer-focused products Familiarity with design systems and component libraries Motion design or animation experience Illustration or icon design experience Basic understanding of HTML/CSS and web design constraints Experience supporting experimentation, conversion optimization, or growth marketing initiatives Experience working in fast-paced startup or scale-up environments Experience art-directing or mentoring junior designers As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale's compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire's base salary. Individual offers may vary based on experience and skill set. US Pay Range $117,750—$153,000 USD Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. We encourage you to help us break that statistic! What We Offer An inclusive, flexible environment where you can be your authentic self. We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life. A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles). Comprehensive group benefits with no waiting period. Take advantage of coverage for health, vision, dental, and more for you and your family! Remote first company