10 hours ago
Remote, United StatesSenior
Base Salary
$163k - $226k/yr
Responsibilities
- Define and drive Tailscale’s internal AI-enablement roadmap with engineering leadership and technical staff.
- Build tools, workflows, and shared practices that help engineers use coding agents effectively and safely.
- Evaluate AI models and coding tools and make recommendations about adoption.
- Partner with engineering and non-engineering teams to identify high-leverage AI opportunities.
- Establish guardrails, code-review practices, and documentation for AI-generated code.
- Measure AI-tool adoption and its impact on engineering velocity and quality, and report findings to leadership.
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 amid ambiguity.
- Product or systems thinking with the ability to identify 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 virtual and in-person social events and access to a corporate co-working program.
- Base salary, equity incentive plan, and comprehensive benefits including health, vision, and dental coverage with no waiting period.
- Employer-funded retirement contributions matching employee contributions dollar-for-dollar up to a maximum annual employer contribution of 0.75% of eligible compensation.
- Annual company retreat, team off-sites, and support for intentional in-person collaboration across Canada, the United States, the United Kingdom, and Singapore.
- $1500 USD annually for professional development, plus mentorship, coaching, and internal promotion opportunities.
- Flexible paid time off and paid parental leave of 20 weeks for birthing parents and 16 weeks for non-birthing parents.
- Company-owned laptop choice, monthly home internet reimbursement, and $500 USD for workstation customization.
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.