Toronto, Canada
Zero-config VPN using WireGuard for secure networks
Tailscale builds a mesh VPN platform on WireGuard for secure, peer-to-peer connectivity across devices and services. It serves developers, teams, IT admins, and enterprises needing simple access without complex VPN setups. This eliminates legacy VPN issues like configuration overhead and poor performance.
Builds and maintains production-grade data models and pipelines supporting reporting, analysis, and company decision-making. The role requires strong SQL and data-modeling expertise, attention to data quality, and the ability to improve complex or manual workflows.
Leads the creation of a strategic enterprise sales organization, personally closes complex opportunities, and builds a team serving organizations with more than 10,000 employees. The role requires 5+ years as a top technology sales representative and a record of winning large SaaS deals.
Product Manager owning Tailscale-native app primitives including TSNet Go library, Rust SDK family, and CLI. Define developer experience, reference architectures, golden paths, and embedding patterns for applications that embed Tailscale connectivity and identity from the start. Requires 6+ years PM or engineering-to-PM experience with developer-facing products.
Software Engineer building and scaling Tailscale’s global networking infrastructure (Funnel, DERP relays, dataplane). Design networking features, troubleshoot complex connectivity issues, maintain global services with SRE/DevOps practices. Requires deep networking expertise, Go experience preferred, and comfort with distributed systems.
Lead and mentor teams of engineers building and operating Tailscale's critical Control Plane production services. Manage 2-3 product pods, provide technical direction, drive hiring and culture, and deliver business outcomes through cross-functional collaboration in a fully remote environment.
Own end-to-end revenue compensation operations including commission processing, audits, and CaptivateIQ administration. Partner with leadership on compensation design, quota modeling, financial analysis, and reporting to drive GTM performance in a high-growth SaaS environment.
Solutions Engineer partnering with sales to drive new Commercial business at Tailscale. Lead technical discovery, solution architecture, demos, POCs, and act as trusted advisor on zero-trust networking and secure connectivity for complex deals.
Product Marketing Manager responsible for customer insights, positioning, messaging, sales enablement materials, competitive analysis, and product launches to drive revenue and pipeline at a remote networking/security company. Requires 5+ years in product marketing or related fields with technical affinity.
Software Engineer building internal AI enablement tools, workflows, and practices at Tailscale to help engineers adopt AI coding agents like Claude and Codex more effectively and safely. Requires 5+ years software engineering experience and daily hands-on fluency with modern AI tools.
Own end-to-end planning and execution of internal company events, offsites, virtual gatherings, rewards/recognition programs, and coworking space relationships to build culture and connection for a distributed hybrid team. Requires 7+ years primary ownership of events at high-growth tech companies plus strong budget and vendor management skills.
Software Engineer on the Dataplane team building and optimizing Tailscale's core client-side networking, VPN, and connectivity features using Go and low-level languages. Requires deep networking expertise (routing, NAT, VPNs) plus experience with distributed systems and low-level OS stacks.
Own day-to-day execution of marketing campaigns at Tailscale: build landing pages, execute email campaigns and high-volume newsletters, coordinate webinars, manage marketing ops/CRM tasks, and deliver performance reporting. Requires 2+ years in marketing operations or demand gen, hands-on HubSpot/Salesforce experience, strong QA and organizational skills.
Senior Customer Account Executive responsible for expanding and renewing existing customer accounts at Tailscale through upsells, education on new features, and driving adoption of their secure networking software. Requires 2+ years closing experience in AE/AM roles, preferably with developer/technical products in a PLG motion, and a track record of exceeding quota.
Senior Customer Support Engineer owning complex post-sales technical escalations for Tailscale's VPN networking product. Requires 4+ years in technical support, deep networking and Go debugging expertise, and the ability to drive issues to resolution or high-quality engineering handoff.
Customer Account Executive responsible for expanding and renewing existing customer accounts at Tailscale by identifying new use cases, educating on features, driving adoption, and partnering with Solutions Engineering, Customer Success, and other teams. Requires up to 1 year quota-carrying experience selling developer/technical products in a PLG motion, with strong pipeline and forecasting skills.
Develop and maintain Tailscale's iOS and Android client applications with a focus on mobile VPN infrastructure. Contribute to shared client code in Swift, Kotlin, and Go while supporting other platforms. Requires 5+ years software development experience and networking knowledge.
Lead the vision, strategy, and roadmap for Tailscale's dataplane platform, owning connectivity, performance, reliability, and operator experiences for networking, edge, and infrastructure products. Requires 10+ years PM experience with deep fluency in networking protocols, NAT traversal, and application-layer routing.
Build and maintain core billing infrastructure at Tailscale, including integrations with Stripe/Metronome, metering and pricing logic for usage-based billing, and ownership of the full product lifecycle for financial systems. Requires backend engineering experience focused on payments or billing, strong Go skills, and knowledge of distributed systems.
Tier 2 Support Engineer handling escalated technical tickets for a distributed SaaS networking product. Requires 4+ years SaaS support experience and strong networking fundamentals.
New Business Account Executive responsible for winning new customers through inbound leads and self-sourced pipeline. Requires 2+ years prospecting/closing experience and technical curiosity. Hybrid role in Denver.
Software engineer on the Strategic Projects team building production-grade AI-native connectivity products from prototypes. Heavy Go, LLM/agent tooling, and production hardening focus.
Backend engineer focused on identity and access management, building authentication features (SSO, OAuth2, SAML, WebAuthn) and SCIM sync capabilities in Go for a distributed systems platform.
Own frontend architecture and platform infrastructure for Tailscale's next-generation web console. Build cross-origin auth systems, unified console platform, and shared tooling for React applications at scale.
Own revenue targets for mid-market accounts by managing renewals, expansions, and net-new deals through outbound prospecting and inbound leads. Requires 3+ years closing experience, technical product sales background, and comfort selling to CTO/CISO-level buyers.
Infrastructure Engineer builds and maintains internal engineering services, improves observability, CI/CD pipelines, and cloud infrastructure using tools like Kubernetes and AWS. Requires experience with distributed systems, infrastructure as code, and operating managed services in a remote environment.
Builds security controls across cloud, Kubernetes, networks, and CI/CD for Tailscale. Audits infrastructure, implements security features in Go/Terraform, and provides threat modeling expertise. Requires cloud security and infrastructure experience.
Software engineer focused on security and privacy, improving Tailscale's security through feature development, audits, threat modeling, and spending 50% time writing code. Requires proficiency in Go or similar, security experience, and deep knowledge of vulnerabilities and cryptography.