Infrastructure Engineer at Tailscale | Remote in Canada

About Tailscale Tailscale builds software that lets people securely connect devices from anywhere. The platform supports a wide range of users, from hobbyists to large enterprises, helping teams protect their networks and share access to internal resources. Founded in 2019, Tailscale operates as a fully distributed team and is backed by investors including Accel, CRV, Insight, Heavybit, and Uncork Capital. Role Overview: Infrastructure Engineer (Remote, Canada) The Infrastructure Engineer will join Tailscale’s engineering team to provide shared engineering services and build tools that help internal business units succeed. This role involves working closely with stakeholders across the company, understanding their needs, and managing projects from start to finish. Collaboration with internal customer-facing teams and product engineering is central, particularly when simplifying workflows and providing data for business decisions. What You Will Do Support internal teams by building and maintaining shared engineering tools and processes. Develop strong working relationships with stakeholders to understand requirements and deliver projects end-to-end. Work alongside customer-facing and product engineering teams to streamline operations and surface key data. Contribute to projects such as: Improving observability with metrics, alerting, logging, and telemetry integration Identifying and implementing continuous deployment improvements Applying infrastructure as code to manage changes in cloud environments Partnering with other engineering teams on cross-functional infrastructure solutions Automating upgrades for managed services and virtual machines Tailscale values adaptability, collaboration, and comfort with asynchronous work. The company seeks someone motivated to help advance the product and work effectively with technically skilled teams in a remote-first setting. Key Responsibilities Work with other engineers to design, develop, test, and document core software components. Take ownership of Tailscale’s services by improving observability, handling incident response, and resolving customer support escalations. Analyze and optimize the efficiency, scalability, and stability of system resources.

About Tailscale Tailscale is redefining the Internet by providing innovative software that effortlessly connects individuals and their devices securely, regardless of location. Our platform is utilized daily by a diverse range of users, from hobbyists to global enterprises, to safeguard their networks and facilitate access to internal tools. Founded in 2019, we are fully remote and proudly supported by prominent investors including Accel, CRV, Insight, Heavybit, and Uncork Capital. Join us in shaping a user-friendly, sensible, and secure future for the Internet.Job DescriptionWe are looking for a skilled Security Infrastructure Engineer to join our product security team. The ideal candidate will drive Tailscale's growth while enhancing its safety protocols. Essential traits include the ability to think critically, collaborate with highly technical teams, and adapt to asynchronous work environments.Key ResponsibilitiesDesign and implement robust security measures across various layers (cloud platforms, operating systems, Kubernetes, networks, CI/CD) to protect against sophisticated threats and insider risks.Enhance Tailscale's security by identifying and executing opportunities for privacy features, bug fixes, and implementing a defense-in-depth strategy throughout our codebase.Conduct thorough audits of Tailscale infrastructure to uncover technical vulnerabilities, devise mitigations or solutions, and oversee their resolution.Support engineering strategies through effective threat modeling and security analysis.Allocate 25-50% of your time to software development in this role, alongside operational and governance security tasks.

About TailscaleTailscale is redefining the internet by providing innovative software that allows secure connections between people and their devices, regardless of their location. Our users range from enthusiasts to large enterprises, all utilizing Tailscale daily to safeguard their networks and facilitate access to internal tools. We envision an internet that is straightforward, sensible, and secure, reminiscent of earlier times. Established in 2019 and operating fully remotely, Tailscale has the support of leading investors including Accel, CRV, Insight, Heavybit, and Uncork Capital.Job DescriptionAs an Implementation Engineer (IE) at Tailscale, you will be the key architect of our customers’ initial experience with our product. Reporting to the Customer Success Engineering Team Lead, you will operate at the nexus of Pre-sales, Support, and Product, focusing on delivering value to our customers. You will oversee a substantial number of accounts across both commercial and enterprise segments, guiding them through the crucial first 30 days of their journey with Tailscale. This role is highly impactful and technical, ideal for someone who possesses intellectual curiosity, empathy, robust networking fundamentals, and a dedication to aiding customers in overcoming intricate connectivity and security challenges. Your aim will be to ensure that Tailscale becomes a vital component of our clients’ infrastructure from day one.

About Tailscale Tailscale is revolutionizing the Internet by providing software that facilitates secure connections between individuals and their devices, regardless of their location. Our platform is utilized daily by everyone from hobbyists to multinational corporations, helping teams of all sizes safeguard their networks and access internal tools seamlessly. Founded in 2019, our fully distributed team is backed by prominent investors including Accel, CRV, Insight, Heavybit, and Uncork Capital, and we are committed to creating a sensible and safe future for the Internet.Job DescriptionWe are on the lookout for a skilled Security Software Engineer to join our product security team. This role is critical for advancing Tailscale’s mission while enhancing user safety. Candidates should possess the ability to think critically, collaborate with highly technical teams, and thrive in an asynchronous work environment.

About Tailscale Tailscale is revolutionizing the Internet by providing innovative software that simplifies secure networking for users and their devices across the globe. Our platform is utilized by individuals ranging from hobbyists to large organizations, enabling them to safeguard their networks, share access to internal tools, and more. Founded in 2019, our fully remote team is supported by leading investors like Accel, CRV, Insight, Heavybit, and Uncork Capital as we strive to create a more intuitive and secure online experience.Job DescriptionWe are in search of a dedicated and talented full-time Software Engineer to join our expanding engineering team. In this role, you will:Contribute to the development of the Tailscale product by enhancing both open-source client code and backend services, focusing on networking features and optimizations.Take charge of the complete product lifecycle, from coding and ideation to strategic decision-making.Collaborate with UX/UI designers and product managers to design features that improve networking capabilities.As a fully remote company in its early stages, we seek a highly motivated individual who can drive product advancements. The ideal candidate will be able to think quickly, work collaboratively with technical teams, and thrive in an asynchronous work environment.

About TailscaleTailscale is pioneering a new era of the Internet by providing software that enables seamless and secure connections between individuals and their devices, regardless of their location. From passionate hobbyists to large multinational corporations, teams of all sizes depend on Tailscale daily to safeguard their networks, facilitate access to internal tools, and more. We are committed to creating a future for the Internet that is straightforward, sensible, and secure, reminiscent of its early days. Established in 2019 and operating fully remotely, we are proud to be backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.Job DescriptionWe are on the lookout for a skilled and enthusiastic full-time Product Growth Engineer to join our dynamic team. As part of the Product Growth engineering team, you will:Contribute to the development of the Tailscale product, including client code and backend services.Own the complete product lifecycle, from code writing to product ideation and strategic decision-making.Collaborate closely with UX/UI designers and product managers to define and shape features.Design and implement experiments to gauge customer engagement and identify growth opportunities.Drive impactful improvements to our growth metrics through both lightweight experimentation and larger-scale product initiatives.Work with data to ensure proper metrics and visibility are established for experiments.Act as an advocate for product-led growth best practices across the entire Engineering, Product, and Design (EPD) team.As a fully remote and early-stage company, we seek a driven individual who can help propel our product forward. Essential skills include quick thinking, collaboration with highly technical teams, and comfort with asynchronous work.Key ResponsibilitiesEngage in cross-functional teamwork: Partner with designers, product managers, and fellow engineers.Innovate through product ideation: Bring creative ideas for product features.Collaborate on client and backend development: Work together on Tailscale product features.Participate in code reviews: Be an active participant in the code review process.Continuous improvement: Focus on enhancing product quality and maintainability.Influence product strategy: Provide technical and growth insights to shape the product roadmap.Prototyping: Develop technical prototypes for potential features.Incorporate user feedback: Use insights from users to inform the development process.

About Tailscale Tailscale is revolutionizing Internet connectivity by providing software that enables secure interconnection among users and their devices, regardless of their locations. From individual enthusiasts to large multinational corporations, teams of all sizes rely on Tailscale daily to safeguard their networks, share access to internal tools, and much more. Our mission is to create an Internet that is easy to navigate, sensible, and secure, reminiscent of its earlier days. Founded in 2019 and operating as a fully distributed team, we are supported by esteemed investors including Accel, CRV, Insight, Heavybit, and Uncork Capital.Job DescriptionWe’re seeking a skilled and technically adept Content Marketing Specialist to join our dynamic marketing team at Tailscale. This role involves close collaboration with sales, product marketing, and other marketing teams to effectively translate product positioning and messaging into engaging content. Ideal candidates should possess a solid understanding of networking infrastructure, developer tools, or enterprise security, and the ability to convey technical features in an easily digestible manner. As we are a fully remote and early-stage company, we welcome individuals who are comfortable working asynchronously and excel in uncertain environments.

About Tailscale Tailscale is revolutionizing the Internet by providing innovative software that seamlessly connects individuals and their devices securely, regardless of their location. From individual enthusiasts to large corporations, teams of all sizes rely on Tailscale daily to safeguard their networks and facilitate access to internal tools. We're committed to creating a simplified, sensible, and secure future for the Internet, reminiscent of its earlier days. Established in 2019 and operating fully remotely, we are supported by notable investors such as Accel, CRV, Insight, Heavybit, and Uncork Capital.Job DescriptionWe are seeking a proactive Analytics Engineer who excels in dynamic, complex environments and possesses a knack for clarifying ambiguity. You will become a vital member of our expanding data team, tackling various high-impact challenges across billing, finance, product, go-to-market (GTM), and business operations.If you are someone who poses insightful questions, delves deep to comprehend operational mechanics, and enjoys converting vaguely defined user issues into efficient, scalable data solutions, we want to hear from you. You will not shy away from questioning norms, re-evaluating processes, or navigating intricate systems. Your work will enhance team performance through pristine models, automated workflows, and dependable data.This position is ideal for an individual with substantial experience in delivering production-grade analytics engineering work, eager to expand their responsibilities and influence as our team grows.

About TailscaleTailscale is at the forefront of redefining the Internet by creating software that simplifies secure connections between individuals and their devices, regardless of their location. Our platform is trusted by a diverse range of users, from individual hobbyists to large enterprises, all utilizing Tailscale daily to safeguard their networks, facilitate access to internal resources, and more. Our mission is to restore the Internet to its former ease, sensibility, and safety. Founded in 2019, we operate as a fully distributed team and are supported by notable investors including Accel, CRV, Insight, Heavybit, and Uncork Capital.Job DescriptionWe are on the lookout for a dedicated and talented Full-time Backend Engineer to join our expanding Control Plane Team. As a vital member of our engineering team, you will:Contribute to the development of the Tailscale product by engaging with both open-source client code and associated backend services.Take charge of the entire product lifecycle, from coding to ideation and strategic decisions.Collaborate closely with UX/UI designers and product managers to define and enhance features.As a dynamic and fully remote organization, we seek a highly motivated individual who can drive the product forward at critical intersections of technology and operations, particularly within the control plane and its supporting services. Being able to adapt quickly, work collaboratively with technically skilled teams, and thrive in an asynchronous environment is crucial.Key ResponsibilitiesCollaborate with a team of engineers to design, develop, test, and document core software components.Develop product features related to our control plane, relay infrastructure, and identity integrations.Demonstrate ownership over running services by ensuring observability, participating in incident responses, and handling customer support escalations.Analyze and enhance the efficiency, scalability, and stability of various system resources.Adopt a security-first approach in both design and implementation.What We Are Looking ForProven experience with distributed systems.Proficiency in the Go programming language.Familiarity with one or more SQL databases.Understanding of networking concepts (IP addressing, routing, etc.).

Join Tailscale as a Go Core Client Engineer and be part of a dynamic team focused on reshaping how users access their networks. In this role, you will contribute to the development of our cutting-edge solutions, ensuring seamless connectivity and security for our clients.

About Tailscale Tailscale is revolutionizing the way the Internet operates by providing innovative software that facilitates secure interconnections between users and their devices, regardless of their location. From individual hobbyists to large multinational enterprises, teams of all sizes rely on Tailscale daily to safeguard their networks, manage access to internal tools, and much more. We envision a future for the Internet that prioritizes ease of use, sensibility, and security, reminiscent of its earlier days. Founded in 2019 and operating as a fully distributed company, we are supported by notable investors including Accel, CRV, Insight, Heavybit, and Uncork Capital.Job DescriptionTailscale is on the lookout for a skilled Commercial Solutions Engineer to collaborate with our Sales team in pursuing new business opportunities with Commercial clients. In this role, you will share responsibility for a portfolio of clients alongside Account Executives, lead technical explorations and solution designs, and serve as a trusted advisor for our customers. This position merges extensive networking and security knowledge with a strong sales background to secure competitive contracts, enhance enablement, and influence product development.

About TailscaleTailscale is revolutionizing the Internet by providing innovative software that simplifies secure connections between individuals and their devices, regardless of their location. We cater to everyone from enthusiastic hobbyists to large multinational corporations, empowering teams of all sizes to safeguard their networks, share access to internal tools, and much more. Our vision is to create a user-friendly, sensible, and secure Internet experience reminiscent of its early days. Established in 2019, we operate as a fully distributed team and are supported by notable investors such as Accel, CRV, Insight, Heavybit, and Uncork Capital.Job DescriptionWe are on the lookout for a dedicated and talented full-time Software Engineer to join our expanding team. In this role, you will collaborate with the engineering team to:Provide vital support to internal business units through shared engineering services and functionalities, crafting the tools and processes that enable their success.Foster relationships with various stakeholders across the organization to understand their needs and manage projects from inception to completion.Work closely with customer-facing internal teams to enhance their operations, taking pride in easing their daily tasks. Collaborate with product engineering to analyze data that informs business decisions.Sample deliverables for this position may include:Implementing new developer tools to boost engineering productivity.Enhancing current tools, such as CI/CD systems.Utilizing production data to identify potential issues.Creating tools for development and staging environments.As a fully remote and early-stage company, we seek a highly motivated individual who can drive product development forward. The ability to think quickly, collaborate with technically adept teams, and work effectively in an asynchronous environment is crucial.Key ResponsibilitiesCollaborate with a team of engineers to design, build, test, and document essential software components.Take ownership of the services that comprise Tailscale’s product by ensuring observability, participating in incident response, and addressing customer support escalations.Evaluate and enhance the efficiency, scalability, and reliability of various system resources.

Join Tailscale as a Software Engineer in our Product Strategy team, where you'll play a pivotal role in shaping the direction of our innovative products. As part of a fully remote team, you'll collaborate with talented engineers and product managers to design, develop, and enhance software solutions that delight our users.In this role, you will have the opportunity to work on interesting challenges, contribute to the overall product vision, and implement features that drive user engagement and satisfaction.

Join Tailscale as a Solutions Engineer specializing in Commercial Expansion Sales. In this dynamic role, you will leverage your technical expertise to drive growth and innovation, working closely with clients to understand their needs and provide tailored solutions. Your contributions will be pivotal in expanding our customer base and ensuring client satisfaction.

Join StackAdapt, a pioneering technology firm dedicated to empowering marketers to effectively engage and convert audiences with unparalleled precision. With an astonishing 465 billion automated optimizations happening every second, our AI-driven StackAdapt Marketing Platform seamlessly bridges the gap between brand and performance marketing, facilitating measurable outcomes throughout the customer journey. Forward-thinking marketers trust StackAdapt to orchestrate high-impact campaigns across programmatic advertising and various marketing channels.As a Senior Quality Engineer specializing in Quality Infrastructure at StackAdapt, you will spearhead the design and implementation of pivotal testing infrastructure projects aimed at enhancing our engineering speed and product reliability. Collaborating closely with Quality Engineering, product engineering, and DevOps teams, you will create robust testing systems and frameworks that empower engineers to develop and deploy with assurance. Your partnership with team leads and architects will be crucial in delivering scalable testing solutions grounded in data-driven insights.Currently, our engineering teams depend on our Quality Engineering infrastructure to uphold quality at scale while enabling swift development cycles. We are transitioning from reactive testing to predictive quality engineering, and your contributions will be vital in constructing the systems that drive this transformation! Discover more about our engineering culture here: https://www.youtube.com/watch?v=LXM2NrkhKZc StackAdapt is a remote-first organization; we welcome candidates from anywhere in Canada for this role. Key Responsibilities:Design and implement intelligent test selection systems that enhance regression testing efficiency and diminish feedback cycles.Develop and uphold scalable test automation frameworks that bolster test reliability and decrease flake rates across our test suite.Collaborate with engineering teams to establish quality gates, streamline CI/CD pipelines, and minimize regression cycle durations.Contribute to initiatives across our Quality Engineering pillars: Prevent, Prove, Observe, and Scale.Create tools and dashboards for test analytics, offering insights into test coverage, reliability metrics, and performance trends.Tackle intricate testing challenges including test parallelization, isolation, and intelligent failure analysis.Share expertise and best practices with the team, promoting enhanced Quality Engineering infrastructure capabilities across the organization.

About TailscaleTailscale is revolutionizing the way the Internet operates by providing software solutions that facilitate secure connectivity between individuals and their devices, regardless of location. Our platform is trusted by a diverse range of users, from enthusiastic hobbyists to large multinational corporations, enabling them to safeguard their networks and conveniently share access to internal tools. Founded in 2019 and operating as a fully distributed team, we are proud to be backed by prominent investors including Accel, CRV, Insight, Heavybit, and Uncork Capital. Join us in creating a more straightforward, sensible, and secure Internet experience.Job DescriptionAs a Customer Success Engineer (CSE) at Tailscale, you will serve as a vital link between our technical capabilities and the needs of our most important clients. Your role will involve working closely with customers to guarantee their successful integration of Tailscale’s products, guiding them through the onboarding process, fostering long-term adoption, and offering expert technical assistance throughout their journey. This position requires a blend of technical expertise, problem-solving abilities, and a customer-centric approach to empower clients to fully utilize Tailscale's capabilities. You will report directly to the VP of Customer Experience.

About UsAt Atolio, we are a pioneering remote startup, backed by seasoned leaders from industry giants like Splunk and PagerDuty. Our mission is to democratize access to organizational knowledge across diverse applications and platforms. As an early-stage company, we leverage modern cloud infrastructure, robust security practices, and meticulous systems design to empower teams developing innovative AI and ML solutions. Our collaborative culture, advanced tooling, and extensive benefits create an environment where ownership, curiosity, and continuous development thrive.About the RoleIn the role of IT Systems Engineer, you will be instrumental in shaping and advancing the internal systems that fuel our security-focused remote technology firm. Your responsibilities will encompass user and device management, endpoint security, SaaS tools, access control, and compliance assistance, all while enhancing reliability, automation, and employee satisfaction.This opportunity is perfect for those who relish the challenge of structuring scalable internal systems, automating workflows through coding, and collaborating closely with engineering and security teams in a dynamic startup atmosphere.What You’ll DoManage user lifecycle across identity providers, devices, GitHub, and SaaS platforms (onboarding, offboarding, role modifications).Enhance endpoint management for our fully remote workforce (macOS and Linux) focusing on security, patching, and compliance.Oversee identity and access management, including SSO systems (e.g., Okta), adhering to least-privilege guidelines.Manage GitHub organization settings, access controls, and repositories while collaborating with engineering teams.Develop and sustain automation for IT workflows using code (e.g., provisioning, access reviews, audits).Refine and maintain internal IT systems with a focus on reliability, scalability, and user experience.Collaborate with security and engineering teams to support compliance initiatives (e.g., SOC 2, ISO 27001), audits, and evidence gathering.Establish and enforce device, access, and security policies while balancing usability and productivity.Assess, implement, and manage SaaS tools utilized across the organization.Lead IT initiatives from conception to execution, including system rollouts, tool migrations, and process enhancements.

Join us at Mechanical Orchard as an Infrastructure Software Engineer, where you will play a crucial role in designing and implementing robust software solutions that enhance our infrastructure capabilities. You will work closely with cross-functional teams to ensure seamless integration and optimal performance of our systems.In this position, you will leverage your technical skills to troubleshoot and resolve complex software issues, while also contributing to the development of innovative solutions that drive our business forward.

Join luxurypresence as a Staff DevOps Engineer in the Developer Infrastructure team! As a key player, you will be responsible for designing and optimizing the development and operations processes, ensuring seamless integration and deployment pipelines. Your expertise will help us enhance our infrastructure while ensuring reliability and performance.This is a fantastic opportunity for a passionate engineer to make a significant impact in a collaborative remote environment.

Join System Canada Technologies as an IT Infrastructure Manager, where you will play a crucial role in overseeing and enhancing the IT infrastructure for government projects. This position offers an exciting opportunity to lead a team of dedicated professionals in a dynamic environment.