10 hours ago
Remote, CanadaSenior
Responsibilities
- Define and drive Tailscale’s internal AI-enablement roadmap with engineering leadership and technical staff.
- Build and iterate on tools, workflows, and shared practices for effective use of coding agents.
- Work with the team building Aperture by Tailscale, an AI gateway used internally and offered as a product.
- Evaluate new AI models and coding tools and recommend which technologies to adopt.
- Identify high-leverage AI opportunities across engineering and non-engineering teams.
- Establish guardrails, review practices, and documentation for safely shipping AI-generated code.
- Support internal AI adoption through advocacy, teaching, and cross-functional collaboration.
- Track adoption and measure the effect of AI tooling on engineering velocity and quality, reporting results to leadership.
Requirements
- At least 5 years of professional software engineering experience.
- Daily, hands-on power-user fluency with modern AI coding tools such as Claude Code, Codex, or Pi.
- Experience building and shipping internal tools or developer-facing automation.
- Strong written and verbal communication, teaching, and internal advocacy skills.
- Comfort with ambiguity and self-directed prioritization on a small, evolving team.
- Product or systems thinking with the ability to identify and prioritize high-leverage opportunities.
- Preferred: experience in developer experience, platform engineering, or internal tooling.
- Preferred: experience evaluating or benchmarking LLMs and coding agents.
- Preferred: experience with Go or Rust in addition to Python.
- Preferred: background in security or code-review practices.
- Preferred: experience in developer relations, technical evangelism, customer-facing developer advocacy, or technical project management.
Benefits
- Flexible, inclusive, remote-first work environment with virtual and in-person social events and corporate coworking support.
- Comprehensive health, vision, dental, and other group benefits with no waiting period.
- Base salary, equity incentive plan, and variable commission for quota-based roles.
- Employer-funded retirement contributions matching employee contributions dollar-for-dollar up to the stated annual limit.
- Annual company retreat, team off-sites, and support for distributed team travel.
- $1500 USD annually for professional development, plus mentorship, coaching, and internal promotion opportunities.
- Flexible paid time off program.
- Company-owned laptop choice between Mac or PC, monthly home internet reimbursement, and $500 USD for workstation customization.
- Paid parental leave top-ups of 20 weeks for birthing parents and 16 weeks for non-birthing parents.
- Fully distributed work across Canada, the United States, the United Kingdom, and Singapore, with some roles requiring in-office collaboration when noted.
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.