Software Engineer, AI Enablement

Tailscale

Software Engineer, AI Enablement at Tailscale enhancing AI-assisted development tools. Collaborating with teams to improve engineering workflows utilizing AI within the company.

Posted 7/24/2026full-timeRemote • California • 🇺🇸 United StatesMid-LevelSenior💰 $163,000 - $226,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates expertise in AI-enablement strategies and internal tool development, with a focus on effective AI practices and measurable impact on engineering velocity. Strong communication skills facilitate collaboration across engineering and non-engineering teams.

Highest-signal resume keywords

5+ Years Software Engineering ExperienceFluency With AI Coding ToolsInternal Tools DevelopmentStrong Communication SkillsProduct Thinking

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Software EngineeringAI Coding ToolsInternal Tools DevelopmentAutomationAI Model Evaluation

Soft Skills

Strong CommunicationInternal AdvocacyComfort With AmbiguitySelf-Directed Prioritization

Tools & Technologies

Claude CodeCodexPi

Industry Keywords

AI PracticesEngineering VelocityHigh-Leverage OpportunitiesDocumentationWorkflows

About the role

Key responsibilities & impact

Partner with engineering leadership to define Tailscale's internal AI-enablement priorities and roadmap.
Work with the team that's building Aperture by Tailscale – our AI gateway.
Build, maintain, and iterate on internal tools, workflows, and shareable practices.
Evaluate new AI models, agents, and tools.
Work directly with both engineering and non-engineering teams to find high-leverage opportunities.
Develop infrastructure, guardrails, review practices, and documentation for safe AI use.
Act as an internal advocate for effective AI practices.
Track adoption and measure the impact of AI tooling on engineering velocity.

Requirements

What you’ll need

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
A balanced approach — trying to get people to use AI effectively and safely
Comfort with ambiguity and self-directed prioritization on a small, still-forming team
Product or systems thinking — able to identify and prioritize high-leverage opportunities

Benefits

Comp & perks

An inclusive, flexible environment where you can be your authentic self.
A competitive total compensation package.
Comprehensive group benefits with no waiting period.
Remote first company —most of our teams work fully remotely.
Employer-funded retirement contributions.
Connect with other Tailscalars IRL.
Support for your personal and professional development.
Paid time off and a healthy work-life integration.
A build-your-own home office setup.
Paid parental leave program.