10 hours ago
Remote, United KingdomSenior
Responsibilities
- Define and drive Tailscale’s internal AI-enablement roadmap with engineering leadership and technical staff.
- Build and iterate on internal tools, developer workflows, and shared practices for effective use of coding agents.
- Work with the Aperture team and partner across engineering and non-engineering teams to identify high-leverage AI opportunities.
- Evaluate models and AI tools and make recommendations about adoption.
- Establish guardrails, review practices, and documentation for safely shipping AI-generated code.
- Track AI tooling adoption and measure its effects on engineering velocity and quality.
- Teach, influence, and support teams in adopting effective AI development practices.
Requirements
- 5+ years of professional software engineering experience.
- Daily, hands-on power-user 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, teaching, and internal advocacy skills.
- Ability to prioritize independently and operate comfortably in an ambiguous, early-stage team environment.
- Product or systems thinking with the ability to identify and prioritize high-leverage opportunities.
- Preferred: experience in developer experience, platform engineering, internal tooling, LLM or coding-agent evaluation, Go or Rust alongside Python, security or code-review practices, developer relations, technical evangelism, customer-facing developer advocacy, or technical project management.
Benefits
- Remote-first, flexible work environment with fully remote work for most teams.
- Health, vision, dental, and other comprehensive group benefits with no waiting period.
- Employer-funded retirement contributions and an equity incentive plan.
- Annual company retreat, team off-sites, and support for distributed collaboration across Canada, the United States, the United Kingdom, and Singapore.
- Professional development support, mentorship, coaching, and internal promotion opportunities.
- Flexible paid time off and paid parental leave.
- Company-owned laptop choice, monthly home internet reimbursement, and home-office setup support.
- Accessible and inclusive hiring process with accommodations available upon request.
About Tailscale
Tailscale builds a software-defined mesh VPN that lets individuals and organizations securely connect devices and services using WireGuard and single sign-on. It sells a subscription SaaS with free and paid plans, offering features like access control lists, device authentication, and admin tooling for teams and enterprises. Founded in 2019 and headquartered in Toronto, the company is privately held and used from hobby projects to corporate networks.