Software Engineer, AI Enablement

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Tailscale

WebsiteLinkedInAll Job Openings

51 - 200 employees

Founded 2020

☁️ SaaS

🔐 Security

📡 Telecommunications

💰 $100M Series B on 2022-05

SaaS • Security • Telecommunications

Tailscale is a company that provides a modern VPN solution founded on WireGuard technology, simplifying networking by creating secure, software-defined networks that connect users, services, and devices with ease. By eliminating the complexities of legacy VPNs, Tailscale offers secure remote access, site-to-site networking, and multi-cloud networking, all while ensuring user-friendly, quick deployment without complex configurations. Recognized for enabling zero-trust environments and seamless workflows, Tailscale supports robust security features such as automated user onboarding, encryption, and access control lists (ACLs). This tool is particularly popular for both enterprise and personal use, praised for its integration capabilities and ease of use, making secure networking accessible anywhere, regardless of infrastructure.

📋 Description

• 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.

🎯 Requirements

• 5+ years of professional software engineering experience • Genuine, daily, hands-on fluency with modern AI coding tools (Claude Code, Codex, Pi, or similar) • Experience building and shipping internal tools or developer-facing automation • Strong written and verbal communication and internal advocacy skills • A balanced approach — trying to get people to use AI effectively and safely where appropriate. • Comfort with ambiguity and self-directed prioritization on a small, still-forming team • Product or systems thinking — able to identify and prioritize high-leverage opportunities.

🏖️ Benefits

• An inclusive, flexible environment where you can be your authentic self. • A competitive total compensation package. • Comprehensive group benefits with no waiting period. • Remote first company —most of our teams work fully remotely. • Employer-funded retirement contributions. • Connect with other Tailscalars IRL. • Support for your personal and professional development. • Paid time off and a healthy work-life integration. • A build-your-own home office setup. • Paid parental leave program.