Tailscale

You would improve operational processes for engineering, product, and design teams, manage bug and incident tracking and project reviews, and analyze data to drive efficiency improvements. | The role requires significant program or technical program management experience in a remote startup working with engineering and product teams, along with data analysis skills and familiarity with Jira and Snowflake. | 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 Program Manager to join our team. This is a tactical, implementation-focused role, hands-on in shaping how EPD (Engineering, Product & Design) operates, works together, and stays productive: building and refining the processes and rhythms that keep the org running, driving improvement initiatives over time, and owning the processes behind EPD's operational health. You'll help the team understand trends and spot where improvements are needed. Because we're an early-stage and fully remote company, we're looking for an individual who can work independently to align the teams involved in building the product. A deep understanding of the technical engineering space (how engineering teams operate, where the friction points typically live, and what good looks like) is essential to being effective and credible in this role. Ability to think on one's feet, enjoy collaborating with highly technical teams, operate comfortably in ambiguity without a clearly defined deliverable, and be comfortable working asynchronously is essential. Key Responsibilities You will work as part of the TPM team to: Own the processes for bug tracking, incidents, reliability, and escalations, and continuously improve them to drive efficiency and progress toward EPD's operational health goals. Spot trends across operational health data and translate them into clear insights on how EPD is doing and where improvement is needed. Build dashboards and reports in tools like Jira and Snowflake that give EPD and the broader company visibility into operational health and progress. Turn data into a clear story: what it's telling us, why it matters, and what needs to change, then design and implement the process changes to act on it. Identify process gaps with EPD and proactively develop just the right amount of process to fill the gap: not too much, not too little. Support planning activities and project tracking processes, helping keep them running smoothly and consistently across EPD. Help run project status reviews, leadership roadmap reviews, and priority reviews, making sure the right information is ready and the right people are in the room. Connect the dots across systems, processes, and teams, spotting where disconnected efforts overlap, conflict, or could be simplified, and acting on it. Jump in on whatever initiative pops up in EPD that needs support, structure, or someone to help carry it forward, whether or not it fits inside a defined program. Handle project retrospectives involving participants and stakeholders to understand what went well and what should be adjusted in future project work. Seek opportunities to bring about ongoing improvement and simplification in business operating procedures and practices, leading to improved efficiency and effectiveness. What We Are Looking For Experience as a Program Manager or Technical Program Manager (TPM), coordinating with stakeholders and cross-functional teams, particularly experience working closely within Engineering and with Product. Experience as a Program/Technical Program Manager in a remote startup environment A deep, working understanding of the technical engineering space, including how engineering teams operate day to day, common workflows and tooling, and where technical and process friction tend to show up. Experience owning operational health processes, such as bug tracking, incidents, reliability, or escalations, and using them to drive measurable efficiency gains. Strong data skills, including building dashboards and reports in tools like Jira and Snowflake, and a solid understanding of how to read and interpret data. Ability to spot trends in data and translate them into a clear story: what's happening, why it matters, and what should change, paired with the ability to design and implement the process changes needed to act on it. Experience supporting planning cycles, project tracking, and recurring reviews, such as project status reviews or leadership roadmap and priority reviews. A comfort level with ambiguity and undefined deliverables. You're motivated by taming chaos and improving how things run, not just shipping a fixed checklist. A tactical, execution-first orientation: you're energized by hands-on implementation and getting things done, more than by high-level strategy or planning alone. Experience working with Engineering, Product, and Design leadership, understanding their motivations and priorities, and using that to help move initiatives forward and communicate goals across the company. Ability to give and process constructive feedback, as well as work independently. Ability to communicate openly, supporting and championing innovation and inclusivity, in both written and verbal communication. Familiarity with Agile methodologies and project management tools, such as Jira, Notion and GitHub. Familiarity with technical solutions, engineering practices, and the security and engineering lifecycle. 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 $114,000—$143,000 USD 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—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description. Employer-funded retirement contributions. Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation. Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration. Support for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities. Paid time off and a healthy work-life integration. Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world! A build-your-own home office setup. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own. Paid parental leave program. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents). Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter. Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people. Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit https://tailscale.com/scam-awareness.

Own the experimentation roadmap, design and run high-impact website tests, set testing standards, and coach cross-functional partners on hypotheses and results. | Requires 6–9 years in conversion optimization or web experimentation, proficiency with experimentation platforms and statistics, technical skills in HTML, CSS, JavaScript, and SQL, and communication with senior stakeholders. | 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 looking for a Senior Web Experimentation Manager to own the experimentation program across Tailscale's highest-traffic website pages, including the homepage, pricing, use-case pages, and paid landing pages. You'll set the roadmap, the test design standards, and the decision rules every experiment runs on, and you'll design and ship the highest-stakes tests yourself. You'll work closely with web strategy, web development, design, product marketing, and analytics partners, and you'll coach the people running tests alongside you. This role is for someone who has run an experimentation program, and not only experiments. You know when a test is the right tool and when a change is better shipped without one. You can hold a decision rule when a result is inconvenient, and you treat a flat result as information. Success means a program the rest of the company trusts, results that hold up to scrutiny, and learnings that change what we build next. Key Responsibilities Own the experimentation roadmap, from taking in ideas across the team to prioritizing them against traffic, expected impact, and cost. Set and maintain the standards every test runs on, including sizing, statistical power, minimum detectable effect, guardrail metrics, and the rules for shipping, iterating, or stopping a test. Review test designs before launch and results before they're shared, so every number we report is one we can stand behind. Design, build, and run the most consequential experiments yourself, particularly on pricing and the homepage. Own the health of our testing platform and measurement with web development and analytics, so tracking works and results reconcile with our analytics data. Maintain the experiment record as the source of truth for what our website has learned, and turn accumulated results into recommendations for web strategy. Report program results to marketing leadership: what we learned, what shipped, and what we're testing next. Coach contributors across web, design, and marketing on hypothesis quality, test design, and reading results correctly. What We Are Looking For 6–9 years of experience in conversion optimization, web experimentation, growth marketing, or a related field, including ownership of an experimentation program across multiple pages or products Deep experience with a testing platform such as Optimizely, VWO, or a comparable tool, including program-level setup and governance Strong command of experiment statistics, including power and sample size, minimum detectable effect, false positive control, guardrail metrics, sample ratio mismatch, and the risks of peeking and multiple comparisons The ability to evaluate a test's design and validity, and to explain plainly why a result should or shouldn't be trusted Comfort with HTML, CSS, and JavaScript to build and debug client-side variations yourself Working proficiency in SQL and an analytics tool such as GA4, enough to validate results independently of the testing platform Sound judgment about when an experiment is the right tool, and when a change is low-risk and reversible enough to ship without one Clear writing and communication, with the ability to present results and tradeoffs to senior stakeholders Experience coaching or mentoring others on experimentation, formally or informally Comfort working in a remote-first, async environment Nice to Have Experience experimenting on pricing pages, or on pages that route visitors between self-serve and sales-assisted paths Experience with B2B SaaS, developer tools, infrastructure, or cybersecurity products Experience with server-side or feature-flag testing, or with Bayesian or sequential testing methods Experience moving an experimentation program from one testing platform to another Familiarity with accessibility and web performance considerations in test builds Experience building an experiment library that other teams use 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 $114,000—$145,000 USD 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—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description. Employer-funded retirement contributions. Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation. Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration. Support for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities. Paid time off and a healthy work-life integration. Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world! A build-your-own home office setup. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own. Paid parental leave program. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents). Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter. Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people. Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit https://tailscale.com/scam-awareness.

You would define the internal AI-enablement roadmap, build developer tools and workflows, establish safeguards for AI-generated code, and measure effects on engineering productivity and quality. | The role requires 5+ years of software engineering experience, hands-on fluency with AI coding tools, developer-facing automation experience, and strong communication skills. | 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. US Pay Range $163,000—$226,000 USD 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—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description. Employer-funded retirement contributions. Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation. Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration. Support for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities. Paid time off and a healthy work-life integration. Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world! A build-your-own home office setup. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own. Paid parental leave program. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents). Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter. Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people. Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit https://tailscale.com/scam-awareness.