Tailscale

AI Engineer

• Partner with engineering leadership to define Tailscale's internal AI-enablement priorities and roadmap.
• Work with the team that's building Aperture by Tailscale – our AI gateway.
• Build, maintain, and iterate on internal tools, workflows, and shareable practices.
• Evaluate new AI models, agents, and tools.
• Work directly with both engineering and non-engineering teams to find high-leverage opportunities.
• Develop infrastructure, guardrails, review practices, and documentation for safe AI use.
• Act as an internal advocate for effective AI practices.
• Track adoption and measure the impact of AI tooling on engineering velocity.

Software Engineer, AI Enablement

• Partner with engineering leadership to define Tailscale's internal AI-enablement priorities and roadmap.
• Work with the team that’s building Aperture by Tailscale – our AI gateway.
• Build, maintain, and iterate on internal tools and workflows.
• Evaluate new AI models, agents, and tools.
• Work directly with both engineering and non-engineering teams to find opportunities to apply AI.
• Develop infrastructure, guardrails, review practices, and documentation for the safe use of AI-generated code.
• Act as an internal advocate for effective AI practices.
• Track adoption and measure the real impact of AI tooling on engineering velocity and quality.
• Expect the day-to-day to span hands-on building, teaching, and prioritization.

• Partner with engineering leadership to define AI-enablement priorities.
• Work with the team building Aperture by Tailscale.
• Build, maintain, and iterate on internal tools and workflows.
• Evaluate new AI models and make recommendations.
• Collaborate with teams to find opportunities to apply AI.
• Develop infrastructure and practices for safe use of AI-generated code.
• Advocate for effective AI practices through documentation and coaching.
• Track adoption and measure the impact of AI tooling.
• Expect varied tasks including building, teaching, and prioritization.

Events

• Planning and running the company-wide offsite - venue, logistics, budget, agenda, and the on-site execution itself.
• Planning team-level events and offsites with team leads, balancing what each team wants against overall budget and timeline.
• Running a regular cadence of virtual events that actually keep a distributed team feeling like one team.
• Managing relationships with coworking providers and physical space vendors, including renewals, capacity planning, and day-to-day issues as they come up.
• Acting as the point person for in-office or coworking space needs - desk capacity, meeting room access, badge/access logistics - so teams can just show up and work.
• Evaluating and recommending new coworking locations as the team grows or shifts geographically.
• Owning rewards and recognition end to end, from the platform itself to nominations and the moments that make people feel seen.
• Improving the remote and hybrid experience generally - swag, onboarding touches, the small rituals that matter when you rarely see the office.
• Sourcing, negotiating with, and managing vendors: venues, caterers, travel, AV, swag, event platforms.
• Owning event budgets from the forecast through reconciliation, and flagging variances before they become a problem.
• Handling the full logistics chain - invites, RSVPs, travel, run-of-show docs, day-of execution, wrap-up - so nothing falls through the cracks.
• Collecting feedback after every event and actually using it to make the next one better.
• Traveling as needed to support offsites and in-person events (roughly 10–25% of the time).

Events Manager

Support Engineer

• 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.

Senior Customer Support Engineer, Customer Escalations

Account Executive

• Become an expert in how Tailscale helps our customers
• Build a credible pipeline every quarter by engaging with clients on upsells and renewals
• Own an upsell and renewal number across your accounts
• Help educate customers on the value of Tailscale throughout the evaluation & adoption cycle
• Generate short-term results while maintaining annual pipeline coverage
• Provide accurate weekly forecasting & revenue delivery
• Create mutual action/success plans with prospective and existing customers where appropriate to help them evaluate and expand their usage of the Tailscale product
• Participation in video-recorded customer meetings is a core part of this role. Recordings are used for training, collaboration, and quality improvement

Senior Customer Account Executive

• Serve as the primary escalation point for technically complex tickets raised by paying customers, taking full ownership through to resolution.
• Diagnose and troubleshoot advanced Tailscale-specific issues like ACL misconfigurations, subnet routing/exit node configurations, and integration with identity providers (e.g. Okta, Azure AD).
• Manage a ticket queue with a consistent focus on SLA adherence, ensuring timely first responses and resolutions.
• Drive positive user outcomes and maintain high CSAT scores by providing clear, helpful, and accurate technical guidance.
• Balance a high volume of daily ticket replies while maintaining the technical depth required to troubleshoot complex networking issues.
• Partner cross-functionally to identify recurring friction points and advocate for improvements to the user experience.
• Own escalations of technically complex tickets from Tier 1, including those originating from free-tier users, ensuring issues beyond Tier 1's scope are resolved efficiently and thoroughly.
• Mentor and support Tier 1 colleagues through ticket reviews, escalation guidance, and documentation contributions.

Customer Support Engineer

Technical Customer Success

• Lead and manage the onboarding process for new strategic customers.
• Offer technical support for customers, diagnosing and resolving issues across Tailscale's platform.
• Conduct QBRs with customers to review usage, success metrics, and future goals.
• Build strong relationships with customers, acting as a trusted advisor.
• Serve as the voice of the customer internally, relaying feedback and insights.
• Work closely with sales, product, engineering, and support teams.
• Develop and maintain a repository of technical documentation, FAQs, and guides.

Customer Success Engineer

Product Manager

• Set the vision and roadmap for the Tailscale dataplane. This includes WireGuard behavior, DERP relay expansion and capacity, subnet routers, exit nodes, and client-side networking with the goal of making connectivity feel automatic and reliable
• Define performance and reliability as customer-facing product requirements
• Own connectivity product strategy end to end: regional expansion, capacity planning, relay health observability, enterprise and private DERP/Peer Relay offerings, and sovereign or regulated deployment requirements
• Drive the roadmap for the operational primitives customers use such as subnet routers, exit nodes, and Peer Relays including deployment topology, high-availability modes, route management UX, and production operational tooling
• Own the application-layer connectivity surface — App Connectors, Services, DNS, and network segmentation — that determines how traffic finds its destination and how AI agents, CI/CD, and Kubernetes workloads reach the SaaS and cloud resources they depend on
• Own the operator control surface: how network engineers and IT admins configure, segment, monitor, and troubleshoot their networks at scale, across both the admin console and the CLI
• Partner closely with the embedded Network Features design lead to turn abstract networking systems into legible, well-reasoned product surfaces
• Own connectivity behavior across the full matrix of NAT types, operating systems, mobile carriers, enterprise firewalls, and the "weird" networks customers actually run, improving both success rates and customer debuggability
• Partner with GTM, Customer Success, and Solutions Engineering on production traffic commitments, regulated deployments, and strategic enterprise deals, turning customer learnings into roadmap priorities
• Represent Tailscale's dataplane externally to enterprise customers, cloud partners, infrastructure vendors, and the networking community as a credible domain authority

Principal Product Manager – Dataplane

Engineer

• Deliver projects related to pricing plans and billing.
• Develop our billing integration with third party services, strengthening our end-to-end billing experience.
• Take ownership of the entire product lifecycle, from writing code to product ideation and strategic decision-making.
• Work closely with UX/UI designers and product managers to shape features.
• Work as part of a team of engineers to design, build, test, and document core billing software components.
• Integrate with third-party billing platforms (e.g., Stripe, Metronome) as needed.
• Develop metering, pricing, and rating logic for usage-based and subscription billing models.
• Ensure accurate tracking and reporting of customer usage data.
• Monitor and maintain billing systems to ensure high availability and data integrity.
• Build automation tools for recurring billing tasks, reconciliation, and reporting.
• Collaborate with product, sales, and finance teams to support custom billing requirements.
• Act as a technical expert in billing-related discussions and planning.
• 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.
• Establish observability, alerting, and error handling across the billing pipeline to ensure high availability and responsiveness.
• Lead incident response and root cause analysis for billing-related issues.

Billing Engineer

• Serve as the primary escalation point for technically complex tickets raised by paying customers.
• Diagnose and troubleshoot advanced Tailscale-specific issues.
• Manage a ticket queue with a consistent focus on SLA adherence.
• Drive positive user outcomes and maintain high CSAT scores.
• Balance a high volume of daily ticket replies while maintaining technical depth.
• Partner cross-functionally to identify recurring friction points.
• Own escalations of technically complex tickets from Tier 1.
• Mentor and support Tier 1 colleagues through ticket reviews.

• Serve as the primary escalation point for technically complex tickets raised by paying customers.
• Diagnose and troubleshoot advanced Tailscale-specific issues.
• Manage a ticket queue with a consistent focus on SLA adherence.
• Drive positive user outcomes and maintain high CSAT scores.
• Balance a high volume of daily ticket replies while maintaining the technical depth.
• Partner cross-functionally to identify recurring friction points.
• Own escalations of technically complex tickets from Tier 1.
• Mentor and support Tier 1 colleagues through ticket reviews.

Sales Engineer

• 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.

Solutions Engineer – Commercial, Expansion Sales

Backend Engineer

• Develop the Tailscale product, contributing to both open source client code and related backend services.
• Take ownership of the entire product lifecycle, from writing code to product ideation and strategic decision-making.
• Work closely with UX/UI designers and product managers to shape features.
• Bring a special focus to building features related to identity and access management.
• Work as part of a team of engineers to design, build, test, and document core software components.
• Develop product features in areas that include our control plane, platform, and identity services.
• Develop features that support a broad range of sign-on functionality, such as SSO, OAuth2, SAML, and WebAuthn.
• Develop and maintain SCIM style capabilities to synchronize users, groups and other attributes from IdPs.
• Exhibit ownership over the running services that comprise Tailscale’s product by building for observability, participating in incident response, and fielding customer support escalations.
• Analyze and improve efficiency, scalability, and stability of various system resources.
• Bring a security-first mindset to both design and implementation.
• Participate in our on-call rotation every x weeks, to triage and mitigate incidents.

Backend Engineer, Identity

Frontend Engineer

• Own the technical direction and architecture of Tailscale’s next-generation web console
• Build frontend infrastructure and platform capabilities that enable multiple Tailscale products to ship within a unified console experience
• Bring a special focus to identity-adjacent frontend systems, including authentication, session management, secure cross-origin integrations
• Define and drive the frontend architecture for Tailscale’s next-generation console
• Design and maintain cross-origin authentication and session infrastructure between the console and other services
• Build and operate a frontend serving platform capable of hosting multiple Tailscale products
• Establish shared infrastructure, conventions, and design patterns that consolidate distinct product experiences into a cohesive console platform
• Create frontend architecture patterns, tooling, and abstractions that enable non-frontend engineers to build accessible, production-quality UI safely and efficiently
• Partner closely with Product Design to turn complex infrastructure and identity concepts into intuitive user experiences
• Collaborate with Growth, Design, Product, and other engineering teams on experimentation and iteration
• Define and improve frontend testing strategy across the console
• Work with infrastructure and engineering tooling teams to improve local development workflows
• Raise the quality bar for frontend engineering across Tailscale through technical leadership, reviews, mentoring, and clear platform guardrails
• Required participation in our on-call rotation every few weeks, to triage and mitigate incidents