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Tailscale

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  • Solutions Engineer (Singapore) - Commercial

    Remote (Singapore)

    remote Salary not disclosed

    Solutions Engineer (Singapore) - Commercial Remote (Singapore) About Tailscale Tailscale is building the new Internet 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. Job Description Tailscale is seeking an experienced, highly technical, and commercially driven Solutions Engineer to partner with Sales in establishing and accelerating our business expansion across the APAC region. Based in Singapore, this individual will serve as our founding Solutions Engineer in the region and will report directly into the VP of Customer Engineering. In this role, you will co-own a regional book of business with AE's, driving complex multi-stakeholder deals, uncovering core organizational pain points, and engineering robust solution architectures. Beyond direct sales engagement, you will be a critical anchor for building out technical engagement across the region and collaborating closely with other newly emerging customer-facing technical teams in Singapore, such as Customer Support. This position sits at the center of technical depth and sharp commercial acumen with a mission to translate platform features into long-term customer trust and measurable business outcomes. Key Responsibilities - Act as the pioneering technical voice for Tailscale in APAC, cultivating market presence,

  • Software Engineer, Networking (Edge)

    Remote (United States)

    remote $163K-$226K

    Software Engineer, Networking (Edge) Remote (United States) About Tailscale Tailscale is building the new Internet 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. Job Description We're seeking a skilled and diligent full-time Software Engineer to join our growing team. You will work as part of the engineering team to: - Utilize extensive network engineering knowledge coupled with software development and SRE/DevOps proficiency to design, construct, and oversee Tailscale's global Funnel and DERP relay infrastructure. - Promote operational excellence and automation to guarantee the scalability, high availability, and performance of hosted services. - Offer architectural guidance and troubleshoot escalated networking problems for customers to address intricate connectivity issues. - Partner with internal engineering and product groups to advance hosted services and clients, ensuring updates provide broad value to our customer base. - Support network connectivity capabilities and features by contributing to the open-source client code and developing the Tailscale product dataplane. Because we're an early-stage and fully remote company, we're looking for a strongly motivated individual who can help move the product forward. The ability to think on your feet, collaborate with highly

  • Software Engineer, Networking (Dataplane)

    Remote (United States)

    remote $163K-$226K

    Software Engineer, Networking (Dataplane) Remote (United States) About Tailscale Tailscale is building the new Internet 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. Job Description We're seeking a skilled and diligent full-time Software Engineer to join our growing team. You will work as part of the Dataplane Engineering Team to: - Contribute to the core client connectivity features of Tailscale by applying a deep understanding of network engineering and software development. - Evolve and enhance the Tailscale connectivity offerings between clients, subnet routers, exit nodes and other integrations with customer network infrastructure. - Provide architectural insights and resolve escalated customer network issues to fix complex connectivity problems. - Collaborate with product management and internal engineering to develop integrated network solutions that prioritize scalability and ease of maintenance while ensuring a superior customer experience. Because we're an early-stage and fully remote company, we're looking for a strongly motivated individual who can help move the product forward. The ability to think on your feet, collaborate with highly technical teams, and comfort working asynchronously are essential. Key Responsibilities - Design, build, test, and document core

  • Business Operations & Strategy Manager

    Remote (United States)

    remote $124K-$180K

    Business Operations & Strategy Manager Remote (United States) About Tailscale Tailscale is building the new Internet 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. Job Description The Business Operations & Strategy team is Tailscale's embedded operator for the most significant cross-functional problems that don't have a natural owner, or that are critical to the long-term success of Tailscale - we diagnose, we implement, and we hand off durable solutions so the company doesn't have to solve the same problem twice. We're looking for someone both highly competent and highly curious -- the kind of person who isn't satisfied with "good enough," and who won't leave a known problem unfixed. We're a small, high-leverage team working at the intersection of commercial strategy, operational infrastructure, and company-wide execution. The scope of this role reflects that mandate: things like commercial strategy, international expansion, improving business systems, pricing architecture - work that's critical enough that someone has to own getting it across the finish line. If you thrive on ambiguity, care deeply about getting things done, and want to see a direct line between your work

  • Engineering Manager, Strategic Projects

    Remote (United States)

    remote $206K-$257K

    Engineering Manager, Strategic Projects Remote (United States) About Tailscale Tailscale is building the new Internet 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. Job Description We're seeking a full-time Software Engineering Manager for our Strategic Projects team. Reporting into our co-founder and Chief Strategy Officer, this team exists to show developers and organizations why Tailscale should be their default connectivity substrate, both for internal infrastructure and for embedding into customer-facing products. Aperture, our identity-aware LLM gateway, is one such initiative. This is an AI-native team. We use coding agents heavily as a force multiplier and expect a manager to be a power user and a coach for others. Our customers demand a high bar on code quality, security, and operational rigour, and we treat that as a reason to use every tool available, including LLMs and coding agents, to ship fast without compromising it. As Engineering Manager you will mentor a small team of senior engineers; partner with the CSO, PM, and reference customers to turn market signals (particularly around AI infrastructure, agentic tooling, and identity-aware networking) into shippable POCs and reference

  • Mid-Market Account Executive

    Hybrid (Denver, Colorado, United States)

    hybrid $200K-$200K

    Mid-Market Account Executive Hybrid (Denver, Colorado, United States) About Tailscale Tailscale is building the new Internet 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. Job Description You will be responsible for helping expand and renew current customer accounts as well as work net-new customer accounts across inbound leads and outbound prospecting. This is a new segment and you will be involved in key groundwork in making this a repeatable and successful motion for Tailscale's ambitious growth goals. You will be expected to own deals end-to-end; working with marketing, product, solutions engineering, and our leadership team to close key logos and drive revenue growth. Key Responsibilities - Own an incremental revenue number each quarter while consistently building pipeline throughout the whole year. - Ensure our existing customers get value out of Tailscale and renew + expand their usage. - Provide accurate weekly forecasting & revenue delivery. - Demonstrate the ability to outbound to net-new customers and generate net-new pipeline. - You own the relationship with customers long term and sell new products as we build them. - Participation in video-recorded customer meetings is

  • Team Lead, Customer Engineering

    Remote (Singapore)

    remote Salary not disclosed

    Team Lead, Customer Engineering Remote (Singapore) About Tailscale Tailscale is building the new Internet 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. Job Description Tailscale is seeking its first hire in Singapore to establish and lead our APAC customer engineering operations. As Team Lead, Customer Engineering in this region, you will serve as a player coach responsible for building a high-performing customer engineering team from the ground up and establishing Tailscale's unique company culture locally. You will manage daily operations for a team of 8-10 Customer Engineers, ensuring world-class service for our APAC users while helping to provide follow the sun coverage for our global customer base. This role reports to the VP of Customer Engineering and requires a technical expert who is equally passionate about solving complex networking problems and mentoring others in a collaborative environment. Key Responsibilities - Serve as the founding regional hire for the Singapore customer engineering team, leading the local expansion and recruitment efforts. - Build and establish Tailscale's company culture and operational standards within the new Singapore region. - Manage day-to-day support operations for a pod

  • Team Lead, Customer Support

    Remote (United States)

    remote $160K-$160K

    Team Lead, Customer Support Remote (United States) About Tailscale Tailscale is building the new Internet 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. Job Description We are seeking a Team Lead, Customer Support to serve as a player-coach responsible for the daily operations and professional growth of a team of 8-10 Support Engineers. You will bridge the gap between frontline technical troubleshooting and strategic alignment, ensuring Support Engineers are engaged and delivering high quality customer support to all of our users. Reporting directly to the VP of Customer Engineering, you will align your team's performance with departmental goals, manage technical escalations, and help serve as a voice of the customer to the broader organization. Key Responsibilities - Manage day-to-day support operations for a team of 8-10 Support Engineers. - Lead the onboarding, technical mentoring, and career coaching for all direct reports. - Conduct regular 1:1s and performance management reviews to ensure team alignment and growth. - Oversee the support queue to ensure SLA/SLO adherence, including response and resolution times. - Act as an internal escalation point for both complex technical issues and

  • Manager, Solutions Engineering - Enterprise

    Remote (Canada)

    remote $335K-$368K

    Manager, Solutions Engineering - Enterprise Remote (Canada) About Tailscale Tailscale is building the new Internet 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. Job Description We are looking for a Manager, Solutions Engineering - Enterprise & Mid-Market to join our rapidly growing team. The Solutions Engineering team partners with customers across the full lifecycle - from pre-sales through post-sales - by helping design, evaluate, and operationalize Tailscale in complex enterprise environments. This role exists to raise the quality of enterprise execution: better discovery, tighter technical evaluations, and clearer articulation of why Tailscale actually matters in a real-world architecture. The team works closely with Sales, Support, and Product, and collaborates deeply with Engineering and Marketing so customer feedback doesn't disappear into a backlog. As Manager of Solutions Engineering, you will act as a true player-coach: showing up on important deals, coaching experienced SEs in real moments, and setting a high bar for how enterprise engagements should be run. If you care about people leadership, enjoy being close to the technology, and want to stay customer-facing while building a high-performing team of smart, self-sufficient

  • Developer Relations Engineer

    Remote (United States)

    remote $143K-$179K

    Developer Relations Engineer Remote (United States) About Tailscale Tailscale is building the new Internet 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. Job Description Tailscale is looking for a Developer Relations Engineer to own and improve the developer experience across Tailscale's expanding product portfolio. You'll help developers understand, adopt, extend, and build with our core VPN/connectivity product, while also shaping how that experience evolves as Tailscale expands into new product areas like secure AI access (Aperture), privileged access management (Border0), and whatever comes next. You're a builder, investigator, and storyteller. You write code, chase technical curiosities all the way down, and turn what you learn into things other developers can use like demos, docs, talks, blog posts, sample apps, workshops, videos, tools, and open source contributions. You build things, break things, explain things, and keep going until the thing you're working on has a name. You're comfortable speaking at conferences and just as comfortable digging through an API, a GitHub issue, or a weird networking edge case until it makes sense. You're probably the kind of person who runs a local AI

  • Senior Product Designer

    Remote (Canada)

    remote $196K-$245K

    Senior Product Designer Remote (Canada) About Tailscale Tailscale is building the new Internet 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. Job Description We are looking for a Senior Product Designer to join the design team at Tailscale. You will work closely with product managers and engineers across our cross-functional teams, focused on the experience of IT administrators, DevOps engineers, and security professionals who use Tailscale to build and manage their organization's network. Your work will center on helping these users set up, monitor, and troubleshoot their tailnets. Your job is to make that process feel as clear and reliable as the product underneath it. The work varies in scale and shape. Some projects are well-defined with a clear user problem to solve. Others are improvements to existing features, small cleanup tweaks, or interaction problems that have been on the backlog for a while. You're comfortable moving between those contexts, bringing the same care and curiosity to a focused UI fix as you would to a larger, more open-ended challenge. Tailscale's design team is small and the company is growing fast. That

  • Staff Product Designer

    Remote (Canada)

    remote $226K-$283K

    Staff Product Designer Remote (Canada) About Tailscale Tailscale is building the new Internet 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. Job Description We are looking for a Staff Product Designer to join the design team at Tailscale. You will primarily partner with the Network Features team, which owns one of the most technically complex and strategically important surfaces in the product: how traffic finds its destination, how networks are segmented and connected, and how operators control that behavior at scale. That spans a wide range. On the user-facing side, Admin users orchestrate their networks by configuring settings related to: subnet routing, exit nodes, App Connectors, Services, and DNS. On the infrastructure side, you'll interface with topics like: traffic steering, high availability, DERP servers, and cloud networking primitives. These are not features with obvious consumer analogues. The users are network engineers, IT administrators, and developers building on top of Tailscale, and the problems they bring are genuinely hard to make simple. At the staff level, scope is not handed to you. You will define where design attention is needed across this space,

  • Mobile Platform Developer

    Remote (Canada)

    remote $218K-$273K

    Mobile Platform Developer Remote (Canada) About Tailscale Tailscale is building the new Internet 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. Job Description We're seeking a talented and motivated full-time Software Engineer to join our growing team. You will work as part of the engineering team to: - Develop the Tailscale product, contributing to client code and backend services. The client code is a mix of modern Swift, Kotlin and Go. Prior Go expertise is not a requirement. - Bring a special focus on our mobile platforms, iOS and Android, while contributing to common code that supports macOS, Windows and other core client platforms. Because we're an early-stage and fully remote company, we're looking for a motivated individual who can help move the product forward. The ability to think on your feet, collaborate with highly technical teams, and comfort working asynchronously are essential. Key Responsibilities iOS and Android development expertise: - Proficiency in Swift, SwiftUI, and/or Kotlin - Unit and integration test development and maintenance - Cross-target code sharing - Familiarity with mobile VPN infrastructure - Providing support for the latest Apple

  • Senior Customer Account Executive

    Hybrid (Denver, Colorado, United States)

    hybrid $150K-$150K

    Senior Customer Account Executive Hybrid (Denver, Colorado, United States) About Tailscale Tailscale is building the new Internet 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. Job Description Join our rapidly growing Sales team where you will play an important role at one of the fastest growing companies in the Developer Security space. As a Customer Account Executive, you will be responsible for helping expand and renew current customer accounts. You will focus on finding additional use cases, educating the client base on new feature releases, and ensuring the successful adoption of Tailscale across all of your existing customer accounts. You will partner closely with the Solutions Engineering team, as well as collaborate with the Customer Success, Support, Marketing, and Product teams. We're an energetic company with a wide variety of backgrounds. We coach each other, share feedback, and collaborate to maximize our performance and earning potential, all the while aligning with our customers' needs. Key Responsibilities - Become an expert in how Tailscale helps our customers. - Build a credible pipeline every quarter by engaging with clients on upsells and renewals. -

  • Manager, Sales Development Representative

    Hybrid (Toronto, Ontario)

    hybrid $158K-$181K

    Manager, Sales Development Representative Hybrid (Toronto, Ontario) About Tailscale Tailscale is building the new Internet 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. Job Description We are looking for a thoughtful, hands-on Manager to lead our Sales Development team. In this role, you will coach and develop a group of curious, motivated SDRs who are responsible for building qualified pipeline for the sales organization. You'll guide their day-to-day execution, help refine our prospecting motions, and partner closely with Sales, Marketing, and Operations to align on strategy, messaging, and highest-value opportunities. If you are passionate about coaching early-career sellers, optimizing prospecting strategies, and helping teams grow in a fast-paced startup environment, we'd love to talk to you. Key Responsibilities - Lead, coach, and mentor a team of Sales Development Representatives with clear goals, actionable feedback, and ongoing skill development. - Become an expert in how Tailscale solves real customer problems, and train your team to articulate that value with clarity and confidence. - Build, refine, and operationalize our prospecting playbook across inbound and outbound channels. - Drive team performance through regular coaching sessions,

  • Go Core Client Engineer

    Remote (Canada)

    remote $218K-$303K

    Go Core Client Engineer Remote (Canada) About Tailscale Tailscale is building the new Internet 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. Job Description We're hiring a Go Core Client Engineer. This remote role is for an engineer who will design, implement, and operate the Go-based shared client code that powers our product. You'll work on core client subsystems: connection management, NAT traversal, control connection, encrypted transport, client lifecycle, and cross-platform runtime. You will be expected to ship end-to-end features, and improve reliability, performance, and observability. Key Responsibilities - Design, implement, test, and maintain core client features in Go: connection orchestration, reconnection strategies, NAT traversal, encrypted transport lifecycle, and sync logic. - Ship end-to-end client work: design, implementation, launch, and observability (metrics, logs, traces). - Diagnose and reduce client performance and reliability issues. - Collaborate closely with product, per-platform clients, and platform teams. - Champion engineering excellence by driving code quality, architectural reviews, and design documentation. - Provide technical leadership and mentorship to other engineers, fostering a culture of learning and knowledge sharing. What We Are Looking For The list below captures

  • Implementation Engineer

    Remote (Canada)

    remote $143K-$170K

    Implementation Engineer Remote (Canada) About Tailscale Tailscale is building the new Internet 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. Job Description As an Implementation Engineer (IE) at Tailscale, you are the primary architect of a customers' first experience with our product. Reporting to the CSE Team Lead, you will sit at the intersection of Pre-sales, Support, and Product with the mission of value attainment for our customers. You will manage a high volume of accounts across commercial and enterprise segments, guiding them through the critical first 30 days of their journey. This is a high-impact, technical role designed for someone with intellectual curiosity, empathy, strong networking fundamentals, and a passion for helping customers solve complex connectivity/security challenges with Tailscale. You will ensure that Tailscale becomes a foundational part of our customers' infrastructure from day one. Key Responsibilities - Own the end-to-end technical onboarding journey for a high volume of accounts, with a relentless focus on ensuring customers reach Time To Value (TTV) in under 30 days. - Provide hands-on guidance for technical configurations, including Identity Provider (IdP) integration, Tailnet administration, ACL

  • Security Infrastructure Engineer

    Remote (Canada)

    remote $218K-$303K

    Security Infrastructure Engineer Remote (Canada) About Tailscale Tailscale is building the new Internet 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. Job Description We're seeking a talented software engineer, specializing in security and infrastructure, to help grow our product security team. We're looking for people who can move Tailscale forward while making it safer to use. The abilities to think on your feet, collaborate with highly technical teams, and be comfortable working asynchronously are essential. Key Responsibilities - Design and build security controls across diverse layers (e.g., cloud platforms, OS, Kubernetes, networks, CI/CD) to defend against sophisticated adversaries and insider threats. - Improve the security properties of Tailscale by identifying opportunities for security and privacy features, bug fixes, defense-in-depth, and implementing them across our codebase. - Audit Tailscale infrastructure for technical security weaknesses, identifying mitigations or solutions, and driving them towards resolution. - Support engineering decisions with threat modeling and security analysis and expertise. - You will spend 25-50% of your time in this role writing software vs purely operational or governance security responsibilities. What We Are Looking For Technical - Expertise

  • Security Software Engineer

    Remote (Canada)

    remote $218K-$303K

    Security Software Engineer Remote (Canada) About Tailscale Tailscale is building the new Internet 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. Job Description We're seeking a talented software engineer, specializing in security and privacy, to help grow our product security team. We're looking for people who can move Tailscale forward while making it safer to use. The abilities to think on your feet, collaborate with highly technical teams, and be comfortable working asynchronously are essential. Key Responsibilities - Improve the security properties of Tailscale by identifying opportunities for security and privacy features, bug fixes, and defense-in-depth, and implementing them across our codebase. - Audit Tailscale features for technical security weaknesses, identifying mitigations or solutions, and driving them towards resolution. - Support engineering decisions with threat modeling and security analysis and expertise. - You will spend at least 50% of your time in this role writing software vs purely operational or governance security responsibilities. What We Are Looking For Technical - Proficiency developing in at least one programming language (Tailscale uses Go) - Proficiency developing for at least one application platform (e.g. iOS,

  • Solutions Engineer - Commercial (Expansion Sales)

    Remote (Canada)

    remote $201K-$268K

    Solutions Engineer - Commercial (Expansion Sales) Remote (Canada) About Tailscale Tailscale is building the new Internet 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. Job Description Tailscale is seeking an experienced Commercial Solutions Engineer to partner with Sales in driving new business for Commercial customers. You will co-own a book of business with Account Executives, lead technical discovery and architecture design, and act as a trusted advisor to customers. This role blends deep networking and security expertise with strong sales acumen to win competitive deals, scale enablement, and influence product direction. Key Responsibilities - Partner with AEs to identify, qualify, and close new Commercial customer opportunities. - Lead technical discovery, solution architecture, demos, and POCs to accelerate decision-making. - Guide complex multi-stakeholder deals, aligning technical and business objectives. - Provide structured feedback to shape product roadmap and GTM strategy. - Build scalable enablement resources, demo environments, and solution blueprints for the SE team. What We Are Looking For - 4/5+ years in a customer-facing SE/SA role within networking or security software - Proven experience co-owning pipeline and influencing quota outcomes with Sales