Software Engineer, AI Enablement

RemoteSeniorPosted Aug 17, 2026

GoPythonRustLLMsAI+10 more

About this role

Join Tailscale's small, high-leverage AI Enablement team to build tools, workflows, and practices that help engineers across the company use AI-assisted development effectively and safely. You'll shape internal AI adoption, work on the Aperture AI gateway, and drive measurable impact on engineering velocity.

Must have

5+ years of professional software engineering experience

Daily hands-on fluency with modern AI coding tools like Claude Code, Codex, or Pi

Experience building and shipping internal tools or developer-facing automation

Strong written and verbal communication and internal advocacy skills

Comfort with ambiguity and self-directed prioritization on a small team

Product or systems thinking to identify high-leverage opportunities

Technologies

PythonGitDockerRESTLinuxJSONSecurityOpen sourceAIRustGoCI/CDLLMsLangChainPrompt engineering

Responsibilities

Partner with leadership to define Tailscale's internal AI-enablement priorities and roadmap

Work with the team building Aperture, Tailscale's AI gateway product

Build and iterate on internal tools and workflows for coding agents

Evaluate new AI models, agents, and tools and make clear adoption recommendations

Work across engineering and non-engineering teams to find high-leverage AI opportunities

Develop infrastructure, guardrails, and review practices for safe AI-generated code use

Act as internal advocate for effective AI practices through documentation and coaching

Track adoption and measure impact of AI tooling on engineering velocity and quality

Benefits

Health insuranceDental insuranceVision insuranceRetirement benefits with matchWellness platform with incentivesCompetitive salary and stock option planFlexible PTOHome office allowanceParental leaveRemote workProfessional development

Amenities

Remote first with corporate co-working program accessAnnual company retreat and team off-sitesChoose own company laptop Mac or PCMonthly home internet reimbursement$500 USD workstation customization stipend$1500 USD annual professional development budgetTeam travel support for intentional in-person collaboration