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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 a Director, APAC Go-to-Market to build and lead our GTM business in Asia Pacific, starting from Singapore. APAC represents an important growth opportunity for Tailscale. We have strong conviction in the region and are looking for a leader who can turn that opportunity into a meaningful, durable business: building pipeline and revenue, developing a strong partner ecosystem, winning strategic customers, and building the team we need to scale. We are looking for someone who has built a region before and wants to do it again from scratch. You will set the APAC go-to-market strategy, determine where and how we invest, recruit and lead our initial regional team, and be directly accountable for commercial results. You will have significant autonomy to determine what Tailscale needs to win in the region. You will also be a hands-on commercial leader. You’ll spend time with customers and partners, help shape and close our most important opportunities, and develop a deep understanding of how technology companies need to go to market differently across APAC. You’ll bring those insights back to our global Sales, Marketing, Product, and Engineering teams and help Tailscale become a truly global company. In this role, you will be able to hire the team you need to succeed. We suspect that will include Sales Development, Account Executives, Solutions Engineering, Customer Engineering, and Partner Marketing, but ultimately we will be open to your recommendation based on expertise. These hires will report directly to you with dotted lines to functional departments in North America and EMEA. You’ll lead that team as a region, while working closely with their functional counterparts elsewhere at Tailscale. This role will report to Tailscale’s President, Kevin Kotecki. Key Responsibilities Own the APAC number. You will be accountable for regional pipeline creation and revenue growth. Establish clear targets, build the plan to reach them, maintain strong forecasting and pipeline discipline, and continuously adjust our approach based on what the data and the market tell us. Build and execute Tailscale’s APAC go-to-market strategy. Determine which markets, customer segments, use cases, and routes to market offer the greatest opportunity for Tailscale. Translate global company strategy into a focused regional plan while recognizing that what works in North America or Europe will not always work in APAC. Build a high-performing regional GTM organization. Recruit, lead, and develop exceptional sellers and other customer-facing talent in the region. Build a team that operates as one APAC organization while remaining tightly connected to its global functional counterparts. Create the culture, operating rhythms, and accountability required for a small regional team to move quickly and perform at a high level. Lead from the front with customers. Personally engage in Tailscale’s most important opportunities in the region. Build relationships with senior technical and business leaders, help the team navigate complex enterprise sales cycles, and serve as executive sponsor for strategic customers. Stay close enough to the market to know why we are winning, why we are losing, and what needs to change. Build Tailscale’s presence in the region. Establish Tailscale as a credible and increasingly visible technology company in APAC. Represent Tailscale with customers, partners, at industry events, and within the broader technology ecosystem. Develop the relationships and market intelligence that allow us to identify opportunities earlier than we otherwise would. Be the voice of APAC inside Tailscale. Build a strong point of view on regional customers, competitors, partners, buying behavior, and market dynamics. Bring that perspective into company decisions about product, packaging, marketing, partnerships, and future investments. Build the region for the long term. We expect the shape of our APAC organization to evolve considerably. Identify what capabilities and investments we need next, make thoughtful resource tradeoffs, and build systems that can scale beyond the first phase of the Singapore office. What We Are Looking For Significant experience in enterprise technology go-to-market, with meaningful experience leading Sales or a broader GTM organization across APAC. You have done this before. You have helped build or materially scale an APAC business rather than only operating within an already mature regional organization. A proven track record of owning and exceeding meaningful pipeline and revenue targets in a B2B technology business. Deep familiarity with the APAC technology market and experience operating successfully across multiple countries and cultures, with particularly strong knowledge of Singapore and Southeast Asia. Established relationships within the regional channel and partner ecosystem, along with a track record of turning those relationships into measurable commercial outcomes. A strong network of exceptional GTM talent in the region. You know what great sellers and SEs look like and have demonstrated that you can attract them to work with you. Experience leading complex enterprise opportunities personally. You are comfortable moving from regional strategy and forecasting into a customer meeting or deal review and materially improving the outcome. Experience selling highly technical products to sophisticated buyers. Experience with infrastructure, networking, security, developer tools, cloud, or adjacent enterprise technology is particularly relevant. Strong commercial judgment and analytical ability. You understand pipeline mathematics, forecasting, unit economics, market prioritization, and where to invest limited resources to produce the greatest return. Strong cross-functional leadership skills. You can lead a regional team while partnering effectively with global Sales, Marketing, Product, Engineering, Customer Success, Finance, and Operations teams that you do not directly manage. Excellent written and verbal communication and strong executive presence with customers, partners, candidates, and internal leaders. A builder’s mindset. You are comfortable with ambiguity, limited infrastructure, and changing plans, and you know how to introduce enough process and structure to improve execution without slowing the organization down. High agency and low ego. You are willing to personally do the work required to establish the region while simultaneously building an organization that will eventually make you less central to every decision. A strong perspective on how technology GTM is changing in the age of AI and what those changes mean for winning customers and building partnerships in APAC. 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. 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—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.

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 As a Forward Deployed Engineer at Tailscale, you’ll be the bridge between our technical capabilities and the needs of our most strategic customers. You will work directly with customers to ensure their success with Tailscale’s products, helping them get onboarded, driving their long-term adoption, and providing expert technical guidance throughout their journey. This role requires a combination of technical proficiency, problem-solving skills, and an empathetic customer-centric approach to ensure customers are fully empowered to leverage the power of Tailscale. The role will report directly to the Team Lead, Customer Success Engineers. Key Responsibilities Lead and manage the onboarding process for new strategic customers, ensuring they quickly understand and adopt Tailscale. Provide training and resources that set customers up for long-term success. Offer technical support for customers, diagnosing and resolving issues across Tailscale's platform. Assist with configuration, integration, and troubleshooting to ensure smooth implementation. Conduct QBRs with customers to review usage, success metrics, and future goals. Use these touchpoints to identify opportunities for deeper engagement and horizontal expansion. Build strong relationships with customers, acting as a trusted advisor. Help customers optimize their use of Tailscale by identifying best practices, and by providing recommendations based on their specific use cases and desired business outcomes. Serve as the voice of the customer internally, relaying feedback and insights to the product and engineering teams to help improve the product and the customer experience. Work closely with sales, product, engineering, and support teams to ensure smooth handoffs, escalate critical issues, and drive customer success across the organization. Develop and maintain a repository of technical documentation, FAQs, and guides to help customers self-serve. Share insights and best practices with both the customer and internal teams. What We Are Looking For 6+ Years in a technical role with minimum 2 years of customer-facing experience (Solutions engineer/architect, Sr. Support Engineer, etc.) Experience working with enterprise customers in a consultative capacity Strong understanding of networking, VPNs, and security principles. Experience with cloud infrastructure (AWS, GCP, Azure) and tools like Docker, Kubernetes, and other DevOps technologies Prior experience in a customer-facing technical role such as Technical Support Engineer, Solutions Engineer/architect, or Customer Success Engineer at a SaaS company Ability to clearly explain complex technical concepts to a diverse audience, from non-technical stakeholders to engineers. Strong written and verbal communication skills are a must Analytical mindset and troubleshooting skills, with the ability to think critically and methodically to resolve complex technical issues A passion for delivering excellent customer service and a strong focus on building long-term customer relationships Ability to manage multiple customer accounts, prioritize tasks, and keep projects on track. Strong time management and organizational skills are key A collaborative mindset and ability to work cross-functionally with product, sales, and engineering teams to deliver customer success 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. For this position, our pay ranges reflect target OTE (on target earnings), inclusive of base salary and variable compensation tied to the attainment of quarterly sales targets. CAN Pay Range (OTE) $201,000—$335,000 CAD 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—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.

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). 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.