Tailscale

Full-stack Engineer

• Build prototypes and POCs that showcase Tailscale for AI agents and tooling.
• Work with reference customers to integrate Tailscale, both for internal adoption and for embedding into their products.
• Create reference architectures and share your work through documentation, open source, community engagement, and conference presentations.
• Rapidly iterate with input from colleagues and reference customers.
• Hold the production bar on prototypes that often graduate into Tailscale's product surface area.
• Light travel required (~10-15%).

Software Engineer, Strategic Projects

• Build prototypes and POCs that showcase Tailscale for AI agents and tooling (MCP gateways, LLM proxies, sandboxes, remote servers, and similar emerging workloads).
• Work with reference customers to integrate Tailscale, both for internal adoption (VPN replacement with identity-aware networking) and for embedding into their products to enable secure customer connectivity.
• Create reference architectures and share your work through documentation, open source, community engagement, and conference presentations.
• Rapidly iterate with input from colleagues and reference customers; turn customer conversations into shippable prototypes and reference designs.
• Hold the production bar on prototypes that often graduate into Tailscale's product surface area, including the security and review practices that wrap around agent-generated code.
• Light travel required (~10-15%): primarily team and company onsites, with occasional conferences or customer visits concentrated in North America with potential trips to EU or APAC.

Business Operations

• Reshaping our pricing and packaging strategy.
• Expanding the company to APAC through Singapore.
• Scoping and sizing new commercial opportunities.
• Driving cross-company AI adoption initiatives.
• Performing deep-dive data analysis to identify opportunities and mitigate challenges.
• Partnering with RevOps to mature our GTM infrastructure.
• Reducing rework and duplication in our business systems.

Business Operations – Strategy Manager

• Reshaping our pricing and packaging strategy
• Expanding the company to APAC through Singapore
• Scoping and sizing new commercial opportunities
• Driving cross-company AI adoption initiatives
• Performing deep-dive data analysis to identify opportunities and mitigate challenges
• Partnering with RevOps to mature our GTM infrastructure
• Reducing rework and duplication in our business systems

Engineering Manager

• Manage a talented, senior team of experienced engineers in a growth-stage startup.
• Drive business outcomes measured by adoption of new platform primitives, customer integrations landed, and influence on Tailscale's roadmap.
• Make major design decisions on prototypes that often graduate into production surface area, and own the quality bar for the team's externally-visible artifacts (reference architectures, open source, talks, customer integrations).
• Set the bar for how this team uses AI coding tools: which agents and workflows the team adopts, what review and security practices wrap around agent-generated code, and how the team sustains a fast cadence without lowering the production bar.
• Hire, nurture, and oversee engineers while fostering a fun, creative, and inclusive atmosphere, including healthy conflict and a culture of candid, kind feedback.
• Collaborate across core platform engineering, security, and go-to-market on projects that span domains and often involve direct customer co-development.
• Drive planning across horizons, balancing fast prototype cycles against longer-arc bets on where connectivity, identity, and AI infrastructure are converging.
• Light travel required (~10-15%): primarily team and company onsites, with occasional conferences or customer visits concentrated in North America with potential trips to EU or APAC.

Engineering Manager, Strategic Projects

Account Executive

• 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 a core part of this role. Recordings are used for training, collaboration, and quality improvement.

Mid-Market Account Executive

Growth Marketing

• Partner with stakeholders across Marketing, Product Marketing, Brand, SEO, Product, and Engineering to plan and execute web initiatives.
• Help shape the website roadmap based on business goals, user behavior, technical opportunities, and performance data.
• Identify opportunities to improve site structure, navigation, content discoverability, and user journeys.
• Lead and support large-scale web initiatives such as content migrations, site restructures, new page launches, CMS improvements, and website refreshes.
• Audit existing website experiences and recommend improvements for usability, scalability, and conversion.
• Ensure projects are clearly scoped, documented, prioritized, and communicated across teams.
• Act as a strategic partner to stakeholders while balancing business needs, technical feasibility, and user experiences.
• Own the website experimentation program using tools like VWO.
• Build and maintain an experimentation roadmap aligned to business priorities and conversion goals.
• Develop hypotheses grounded in user behavior, analytics, qualitative feedback, and business context.
• Launch A/B tests, multivariate tests, personalization campaigns, and UX experiments focused on improving sign ups, conversion rates, user engagement, CTA performance, navigation flows, and landing page performance.
• Analyze experiment results and communicate insights, recommendations, and next steps to stakeholders.
• Partner with analytics and engineering teams to ensure accurate tracking, measurement, and reporting.
• Create a culture of evidence-based decision making through experimentation and iterative improvement.
• Translate business goals into actionable web strategies and experiment plans.

Web Strategy – Growth Manager

Developer Relations

• Build and maintain demos, sample apps, reference architectures, tutorials, and technical tools that help developers understand what they can do with Tailscale.
• Create technical content for developers, including blog posts, docs, videos, talks, workshops, livestreams, and conference sessions.
• Represent Tailscale at events, conferences, meetups, community moments, and developer-facing conversations.
• Work closely with engineering, product, marketing, support, and community teams to identify developer friction and turn that feedback into better product experiences.
• Help developers understand Tailscale’s core connectivity product, as well as newer product areas such as secure AI access, privileged access management, identity, infrastructure security, and developer tooling.
• Contribute to open source projects, examples, and integrations where it makes sense.
• Participate in public technical conversations through GitHub issues, pull requests, community forums, social channels, and other developer feedback loops.
• Help define what great developer experience looks like at Tailscale, from first touch to production usage.

Developer Relations Engineer

Platform Engineer

• Develop the Tailscale product, contributing to client code and backend services.
• 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.

Mobile Platform Developer

• Develop the Tailscale product, contributing to client code and backend services.
• Bring a special focus on our mobile platforms, iOS and Android.
• Collaborate with highly technical teams and work asynchronously.

Infrastructure Engineer

• Support and enable internal business units through shared engineering services and functionalities, building the tools and processes for those teams to succeed.
• Build relationships with multiple stakeholders across the organization to understand and meet their needs with projects you'll own end to end.
• Work directly with internal customer facing teams to empower their mission and take pride in making their day-to-day lives easier. Work with product engineering to extract the data needed to drive business decisions.
• Improve observability through metrics, alerting, logging and telemetry integration
• Identify and build improvements for Continuous Deployment
• Utilize infrastructure as code to make changes in a cloud environment
• Collaborate with other engineering teams to build cross functional infrastructure improvements
• Automate upgrades for managed services and VMs.

Brand Designer

• Design high-quality web experiences
• Design landing pages, feature pages, and campaign experiences that are visually compelling and easy to use.
• Apply strong hierarchy, layout, and interaction thinking to improve clarity and user flow.
• Balance brand expression with usability and performance goals.
• Understand and apply accessibility and inclusive design principles.
• Work within and extend our design system to create reusable, scalable components.
• Improve templates, layouts, and patterns used across the site.
• Ensure consistency while evolving the brand for digital environments.
• Own moderately complex projects and initiatives end-to-end, not just tasks, with guidance from Brand Design Lead.
• Surface project ambiguity early and identify potential blockers, proactively proposing actionable solutions.
• Prioritize deadlines effectively, balancing speed, quality, and craft to consistently deliver polished, production-ready assets across digital and print.
• Maintains organized component and asset libraries that scale across the team, enabling others to easily adopt and build on established systems.
• Collaborate with the growth team on testing and improving page performance.
• Thoughtfully iterate on designs based on data, feedback, and evolving priorities.
• Proactively identify opportunities to improve user experience across key journeys.
• Partner closely with web developers to ensure designs translate cleanly into production with minimal to no rework.
• Work with marketing and content teams to bring campaigns and narratives to life across multiple platforms: print, digital, and motion.