Software Engineer, AI Enablement

🕒 July 24

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

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

💵 $218.4k - $302.8k / 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 the 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 for effective coding-agent use • Evaluate new AI models and tools and decide what to adopt • Partner with engineering and non-engineering teams to identify high-leverage AI opportunities • Establish guardrails, review practices, and documentation for safely shipping AI-generated code • Advocate internally for effective AI practices without mandating a single tool • Track adoption and measure AI tooling’s impact on velocity and quality • Report results to leadership

🎯 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 • Ability to teach, write, and influence engineers with different comfort levels 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 and ability to identify and prioritize high-leverage opportunities • Nice to have: prior experience in developer experience, platform engineering, or internal tooling • Nice to have: experience evaluating or benchmarking LLMs and coding agents • Nice to have: experience with Go or Rust in addition to Python • Nice to have: background in security or code-review practices • Nice to have: experience in developer relations, technical evangelism, or customer-facing developer advocacy • Nice to have: technical project management experience

🏖️ Benefits

• An inclusive, flexible environment where you can be your authentic self • A competitive total compensation package including a base salary and an equity incentive plan • Comprehensive group benefits with no waiting period, including health, vision, dental, and more for you and your family • Remote-first work environment • Virtual and in-person social events • Corporate co-working program • Employer-funded retirement contributions matching contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of eligible compensation • Annual company retreat and team off-sites • $1500 USD annually for professional development • Mentorship, coaching, and internal promotion opportunities • Flexible paid time off program • Company-owned laptop (Mac or PC) • Monthly home internet reimbursement • $500 USD home office customization allowance • Paid parental leave top-ups: 20 weeks for birthing parents and 16 weeks for non-birthing parents