Tailscale

• Set the vision and roadmap for the Tailscale dataplane. • Define performance and reliability as customer-facing product requirements. • Own connectivity product strategy end to end. • Drive the roadmap for the operational primitives customers use. • Own the application-layer connectivity surface. • Own the operator control surface. • Partner closely with the embedded Network Features design lead. • Own connectivity behavior across the full matrix of NAT types. • Partner with GTM, Customer Success, and Solutions Engineering. • Represent Tailscale's dataplane externally to enterprise customers, cloud partners, and the networking community.

• 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

• 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.

• 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. • Work closely with finance, product, support, and engineering teams to support accurate billing, revenue reporting, and customer inquiries. • 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.

• Develop the Tailscale product, contributing to client code and backend services. • Bring a special focus on our Windows platform, building and maintaining our Windows client. • Work with engineers on a native Windows desktop client using Windows App SDK, WinUI, C#, XAML and Go. • Implement support for the latest Windows platform features. • Develop and optimize product features on Windows, with a focus on UI components and platform integration. • Develop and maintain unit and integration tests using Microsoft Testing Platform v2 and xUnit. • Contribute to common, cross-platform Tailscale code.

• Develop the Tailscale product, contributing to client code and backend services • Bring a special focus on our Windows platform, building and maintaining our Windows client using WinUI/Windows App SDK stack • Implement support for the latest Windows platform features while maintaining compatibility with older versions • Develop and optimize product features on Windows, focusing on UI components and platform integration • Develop and maintain unit and integration tests using Microsoft Testing Platform v2 and xUnit • Contribute to common, cross-platform Tailscale code

• 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.

• 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.

• 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.

• Own discovery and design on problems that don't always come with a clear brief, from early framing through delivery and QA. • Work closely with engineers and PMs to move from a fuzzy problem to something well-reasoned and shippable. • Deliver across surfaces, GUI and CLI alike, and stay engaged through implementation, not just handoff. • Treat feedback as part of the work, not a checkpoint. Seek it out from peers, your team, and your manager, and use it to make the work better. • Take initiative in how you collaborate and push for clarity, even on projects you're not leading. • Understand the product areas you touch well enough to know when a decision has implications beyond the immediate problem. • Use AI tools where they actually help, synthesizing research, exploring directions faster, pressure-testing ideas.