For teams who want secure, private networks without weeks of setup and configuration, Tailscale makes it easy. Unlike existing corporate VPNs, Tailscale has no upfront cost, minimal latency, and works with their existing services.

Tailscale

Equity / Stock Options

Remote Stipend / Home Office Budget

Paid Time Off

Paid Parental Leave

401(k) / Pension

Learning & Development Budget

Medical, Dental & Vision Insurance

Commission

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.

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 Zach Buchheit, Team Lead, Customer Success Engineers.

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.

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.

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!

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!

—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.

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! 

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. 

. 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 

Experience Requirement

Tailscale is hiring a Forward Deployed Engineer to serve as the technical bridge for strategic customers. The role focuses on onboarding, technical support, and driving long-term adoption using networking, cloud infrastructure (AWS, GCP, Azure), and DevOps tools like Docker and Kubernetes. This position ensures customers are empowered to leverage Tailscale's secure interconnectivity software.

Customer Success

Remote (United States)

Remote (Canada)

Remote (United States) 

Forward Deployed Engineer

Full Time

Tailscale is hiring a Forward Deployed Engineer to serve as the technical bridge for strategic customers. The role focuses on onboarding, technical guidance, and troubleshooting using networking, cloud infrastructure (AWS, GCP, Azure), and DevOps tools like Docker and Kubernetes to drive long-term adoption.

Health Insurance

Co-working

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 Support Engineer (Tier 3), Customer Escalations

 to join our Escalation Engineering 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 Senior Customer Support Engineer (Tier 3), Customer Escalations, you'll partner closely with Support 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 Escalations Team Lead.

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

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

Tailscale is seeking a Senior Customer Support Engineer (Tier 3) for their Customer Escalations team. The role involves owning high-severity technical escalations, performing deep-dive investigations into networking issues, and collaborating with engineering to resolve complex bugs. Key technologies include Go, Python, Linux, and advanced networking concepts like WireGuard and Kubernetes.

Customer Support

Customer Reliability Engineer

Senior Customer Support Engineer (Tier 3), Customer Escalations

Dental & Vision

Tailscale is seeking a Senior Customer Support Engineer (Tier 3) for their Customer Escalations team. The role involves owning high-severity technical escalations, performing deep-dive investigations, and partnering with engineering to resolve complex bugs. Key technologies include Go, Python, Kubernetes, and advanced networking concepts.

We’re looking for a collaborative and analytical Product Marketing Manager to join the marketing team at Tailscale. You will work closely with product, marketing, and revenue teams to identify customer needs, pain points, and articulate “Why Tailscale?” and then turn these insights into actionable assets for us to go-to-market with. This role might be perfect for you if you are familiar with PAM, networking infrastructure, or enterprise security needs, and can communicate technical features as easy-to-digest benefits. If you love highly cross-functional work and want to help a rapidly growing sales and revenue team succeed, read on.

Because we’re an early-stage and fully remote company, we’re looking for a motivated individual who is comfortable working asynchronously, thrives in ambiguity and has a focus on getting it right, not being right.

Becoming the expert on our users and customers — who they are, what their pain points are, and what drives them to seek out solutions 

Collaborating with sales, product and marketing teams to develop and refine product positioning, messaging, and effective content

Launching new products or features, managing cross-functional projects associated with that launch, and measuring revenue and pipeline generated

Creating sales collateral and enablement materials— slide decks, one-pagers, training sessions, customer case studies, webinars, etc.. This includes delegating and working with designers/web developers/content marketers as needed.

Performing competitive and market analysis to inform messaging and campaigns, and influence product strategy

Represent PMM at industry events by delivering demos and gathering firsthand customer and prospect insights to shape messaging and campaign strategy

At least 5+ years of experience in product marketing, working with sales teams, and sales enablement

A proven track record in marketing, product marketing, sales enablement, product management, or a related field with a minimum of 5+ years of direct experience 

An affinity for complex, highly technical subjects

Experience managing interdependent, complex projects and keeping multiple work streams on track

An analytical and data-driven mindset with an enthusiasm for problem-solving and measuring the effectiveness of your work

The ability to quickly adapt and react to changing plans and ambiguity. 

Excellent people skills - this role will interact with many cross-functional teams and the ability to communicate and negotiate effectively will be critical to the success of this role

A bias toward action, execution, and iteration

Experience with networking or security products used in SaaS or cloud environments

Tailscale is seeking a Product Marketing Manager to join its fully remote team. The role involves collaborating with product and revenue teams to develop positioning, messaging, and sales collateral for networking and security infrastructure. Key responsibilities include managing GTM launches and performing competitive market analysis.

Marketing

Product Marketing Manager

Tailscale is seeking a Product Marketing Manager to join its fully remote team. The role involves collaborating with product and revenue teams to develop positioning, messaging, and sales collateral for networking and security products. Key responsibilities include managing GTM launches and performing competitive market analysis.

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.

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.

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

Strong networking fundamentals (TCP/IP, DNS, routing, firewalls) and troubleshooting skills

Deep understanding of zero-trust networking, secure connectivity, and IAM integrations (SSO, SAML, OIDC)

Understanding of AI gateway and governance platforms for centralized LLM access, usage visibility, and audit 

Familiarity with privileged access management (PAM) including session recording, just-in-time access, and protocol-aware controls (e.g., Border0, CyberArk, Teleport)

Experience with infrastructure as code tools such as Terraform, Pulumi, Ansible, or CloudFormation

Hands-on architecture experience with AWS, GCP, and/or Azure

Excellent communication skills, capable of translating technical features into business value

Experience thriving in high-growth or startup environments

Tailscale is seeking a Commercial Solutions Engineer to partner with Sales in driving new business. The role involves leading technical discovery, architecture design, and POCs for commercial customers, leveraging expertise in networking, zero-trust security, and cloud infrastructure (AWS, GCP, Azure).

Sales

Solutions Engineer - Commercial (Expansion Sales)

Company Events

Tailscale is seeking a Commercial Solutions Engineer to partner with Sales in driving new business for Commercial customers. The role involves leading technical discovery, solution architecture, and POCs, requiring deep expertise in networking, zero-trust security, and cloud infrastructure tools like Terraform and AWS.

Join our Strategic Projects team, reporting to the team's Engineering Manager and ultimately 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 every engineer to be a power user. 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.

We move fast from idea to prototype, and we're growing the side of the team that's energized by the path from prototype to dependable product. You'll work shoulder-to-shoulder with product-minded engineers from the moment an idea takes shape, shaping how it's built so it holds up later, and co-owning the work of making it production-grade: stable, observable, maintainable, and ready for real customer load. You're the kind of engineer who finds the long tail of development genuinely satisfying, the edge cases, the failure modes, the tests and runbooks, the details that turn a sharp demo into something customers can rely on.

You'll work directly with reference customers on integrations and own the production bar on prototypes that graduate into Tailscale's product surface area, ensuring the security, review, and operational practices that wrap around agent-generated code actually hold in production.

Tailscale is fully remote, this team operates with significant ambiguity, and the shipping cadence is fast. Comfort working asynchronously and collaborating with highly technical customers is essential.

Partner with product-minded engineers from the start, shaping prototypes (MCP gateways, LLM proxies, sandboxes, remote servers, and similar emerging workloads) so the path to production is built in, not bolted on.

Co-own the journey from "works in a demo" to "stable in production": hardening, error handling, observability, and operational tooling.

Own the production bar on prototypes that graduate into Tailscale's product surface area, including the security and review practices that wrap around agent-generated code.

Work with reference customers to integrate Tailscale, both for internal adoption (VPN replacement with identity-aware networking) and for embedding into their products, with particular attention to reliability, maintainability, and long-term supportability.

Find and close the long-tail gaps, edge cases, regressions, flaky behavior, missing tests, undocumented operational knowledge, that separate a prototype from a dependable product.

Establish and maintain the review, testing, and security practices that let the team ship agent-generated code fast without compromising the production bar.

Light travel required (<10%): primarily team and company onsites, with optional conferences or customer visits concentrated in North America.

Ideal candidates will have experience taking software from prototype to production in startup-like environments. We don't expect expertise with every aspect listed below. Let us know where you feel you have the most experience and where you'd like to keep developing.

Strong at hardening, stabilizing, and maintaining production software; you take satisfaction in detail-oriented work and in closing the long tail of bugs, edge cases, and operational gaps.

Go experience is a must; comfort integrating third-party APIs; basic networking.

Heavy daily use of coding agents (Claude Code, Cursor, or similar) and LLMs in your engineering workflow, with a point of view on where they accelerate work, where they fail, and especially how to wrap them in the review, testing, and security practices that hold the production bar.

Enjoy collaborating closely with exploratory, product-minded engineers and jointly owning the work of getting something solid into production.

Comfort with the cadence of a strategy team at an early-ish startup: priorities shift with market signal, prototype-to-production timelines are short, and the bar on what ships stays high regardless.

Thrive working independently in a remote environment.

Experience operating production services: observability, on-call, incident response, performance and reliability work.

Validating prototype code for production use alongside security teams.

Identity infrastructure: IdP platforms, identity sync/provisioning, directory services; authentication protocols (OAuth, OIDC, SAML, SCIM); access control models (RBAC/ABAC), session management, MFA, passwordless auth.

Building applications on top of LLMs and agentic systems (not just using them as dev tools).

Familiarity with Tailscale itself and with networking challenges in multi-cloud and hybrid deployments.

Open source community participation; experience producing publicly-visible artifacts (blog posts, talks, reference implementations).

Work shoulder-to-shoulder with sharp engineers to turn promising prototypes into products customers depend on.

Work alongside reference customers on real integrations rather than abstract roadmaps.

Shape emerging AI connectivity standards and Tailscale's product strategy.

Collaborate with a small team of motivated, sharp, and fun engineers in a fast-paced, dynamic environment.

Travel Required

Tailscale is seeking a Software Engineer for its Strategic Projects team to transition AI-native prototypes into production-grade products. The role involves hardening software, improving observability, and integrating third-party APIs. Primary technologies include Go, LLMs, and coding agents like Cursor and Claude Code.

Strategic Projects

Software Engineer, Strategic Projects

Tailscale is seeking a Software Engineer for its Strategic Projects team to transition AI-native prototypes into production-grade products. The role involves hardening software, implementing observability, and working with reference customers using Go and LLM-based coding agents. You will focus on security, reliability, and operational rigour for emerging connectivity workloads.

Bonus

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.

Strong networking fundamentals (TCP/IP, DNS, routing, firewalls) and troubleshooting skills.

Deep understanding of zero-trust networking, secure connectivity, and IAM integrations (SSO, SAML, OIDC).

Familiarity with privileged access management (PAM) including session recording, just-in-time access, and protocol-aware controls (e.g., Border0, CyberArk, Teleport).

Experience with infrastructure as code tools such as Terraform, Pulumi, Ansible, or CloudFormation.

Hands-on architecture experience with AWS, GCP, and/or Azure.

Excellent communication skills, capable of translating technical features into business value.

Experience thriving in high-growth or startup environments.

Tailscale is seeking a Commercial Solutions Engineer to partner with Sales in driving new business. The role focuses on leading technical discovery, solution architecture, and POCs for networking and security software. Candidates should possess deep expertise in zero-trust networking, IAM integrations, and infrastructure as code.

Solutions Engineer - Commercial (New Business)

Tailscale is hiring a Commercial Solutions Engineer to drive new business by partnering with Account Executives. The role focuses on technical discovery, solution architecture, and POCs, requiring deep expertise in networking, zero-trust security, and cloud infrastructure across AWS, GCP, and Azure.

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.

Tailscale is looking for an experienced Brand Designer to help bring our brand to life across every customer touchpoint. You'll create thoughtful, high-quality creative that helps people understand our products, builds trust with technical audiences, and supports some of our most important marketing initiatives.

This role reports to the Team Lead and partners closely with Brand, Growth, Web, Content, Product Marketing, and Developer Relations. You'll own projects from concept through execution, contribute to the evolution of our design systems, and help us scale creative output without sacrificing quality.

We're looking for someone who cares deeply about craft, thrives in collaborative environments but is able to work autonomously while requiring minimal direction, and enjoys solving complex communication problems through thoughtful design.

Own brand design projects from creative brief through final delivery with limited guidance

Design high-quality creative assets across web, campaigns, events, social media, presentations, product marketing, and internal communications

Apply and thoughtfully extend Tailscale's visual identity across new formats and channels

Create reusable templates, design systems, and creative processes that improve consistency and efficiency

Partner closely with Growth, Web, Product Marketing, Content, and Developer Relations to deliver cohesive customer experiences

Present design concepts and rationale to stakeholders and thoughtfully incorporate feedback

Balance multiple projects while consistently delivering polished, production-ready work

Contribute ideas that improve the quality, scalability, and effectiveness of our creative work

3+ years of professional experience in brand, marketing, or visual design

Strong portfolio demonstrating exceptional design foundations: color theory, accessibility, typography, layout, and storytelling

Fluency in Figma and Adobe Creative Cloud 

Experience designing for digital marketing, websites, campaigns, and brand systems

Strong understanding of production-ready design across digital and print

Excellent communication and presentation skills

Ability to manage multiple projects and priorities with minimal oversight

Experience collaborating cross-functionally with marketers, writers, developers, and other designers

Strong attention to detail with a high bar for quality and consistency

Comfortable giving and receiving constructive design feedback

Tailscale is seeking a Brand Designer to create high-quality creative assets across web, campaigns, and social media. The role involves owning projects from concept to execution, evolving design systems, and collaborating cross-functionally. Primary tools include Figma and Adobe Creative Cloud to support marketing initiatives and technical audiences.

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