Software Engineer, AI Enablement

🕒 July 24

🌐 United States, Canada, +1 more countries – Remote

🇺🇸 United States – Remote 🇨🇦 Canada – Remote 🇬🇧 United Kingdom – Remote

💵 $163k - $226k / year

⏰ Full Time

🟡 Mid-level

🟠 Senior

🤖 AI Engineer

👻 Ghost score 40%

What it means: how likely this posting is sitting open without active hiring.How to read it: 60% or higher means we think this is a ghost. Lower scores are less of a worry.How we score it: age, reposts, open roles vs team size, how fast jobs close, and whether pay is listed.Fine print: an estimate from public data, not a judgment of the company. Real jobs can score high, so treat it as a hint, not a fact.

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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 and technical staff to define and drive Tailscale's internal AI-enablement roadmap • Work with the team building Aperture by Tailscale, an AI gateway used internally and offered as a product • Build and iterate on tools, workflows, and shared practices that help engineers gain value from coding agents • Evaluate new AI models and tools and determine what Tailscale should adopt • Partner with engineering and non-engineering teams to identify high-leverage AI opportunities • Help other teams ship faster through AI enablement • Establish guardrails, review practices, and documentation for safely shipping AI-generated code • Advocate internally for effective AI adoption without mandating a single tool • Track adoption and measure AI tooling's impact on velocity and quality • Report AI enablement results to leadership

🎯 Requirements

• 5+ years of professional software engineering experience • Genuine, daily, hands-on fluency with modern AI coding tools such as 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 • Ability to teach, write, and influence engineers with varying levels of comfort with AI tooling • Balanced approach to using AI effectively and safely where appropriate • Comfort with ambiguity and self-directed prioritization on a small, still-forming team • Product or systems thinking, with ability to identify and prioritize high-leverage opportunities • Prior experience in developer experience, platform engineering, or internal tooling • Experience evaluating or benchmarking LLMs and coding agents • Experience with a systems language such as Go or Rust, in addition to Python • Background in security or code-review practices • Experience in developer relations, technical evangelism, or customer-facing developer advocacy • Technical project management experience

🏖️ Benefits

• An inclusive, flexible environment where you can be your authentic self • Competitive total compensation package including a base salary, equity incentive plan, and variable commission for quota-based roles • Comprehensive group benefits with no waiting period, including health, vision, dental, and more for you and your family • Remote-first work environment with flexible work arrangements • Virtual and in-person social events • Corporate co-working program through WeWork or similar spaces • Employer-funded retirement contributions matching employee contributions dollar-for-dollar, up to 0.75% of eligible compensation annually • Annual company retreat and team off-sites • $1500 USD annually for professional development • Mentorship, coaching, and internal promotion opportunities • Flexible paid time off • Company-owned laptop choice of Mac or PC • Monthly home internet reimbursement • $500 USD home office workstation customization allowance • Paid parental leave top-ups: 20 weeks for birthing parents and 16 weeks for non-birthing parents • Accessible and inclusive hiring process with accommodations available