Remote opportunity at
TailscaleSoftware Engineer, AI Enablement
Tailscale makes it easy and secure for people and their hardware to connect, wherever they happen to be. Started in 2019 with a remote-only structure, the…
Career Tools
About This Role
Tailscale makes it easy and secure for people and their hardware to connect, wherever they happen to be. Started in 2019 with a remote-only structure, the company says organizations of every size use it to protect networks and share internal tools. Among its backers are Accel and CRV, along with Insight, Heavybit and Uncork Capital. Tailscale is recruiting a Software Engineer focused on AI enablement, whose mission is to help…
Job Description
Tailscale makes it easy and secure for people and their hardware to connect, wherever they happen to be. Started in 2019 with a remote-only structure, the company says organizations of every size use it to protect networks and share internal tools. Among its backers are Accel and CRV, along with Insight, Heavybit and Uncork Capital.
Tailscale is recruiting a Software Engineer focused on AI enablement, whose mission is to help engineering get more out of AI-assisted development. The role reports to a co-founder and sits alongside the company's first engineer dedicated to AI enablement. It is positioned as a foundational job with wide latitude to define what AI enablement should look like as the company scales.
The work involves creating the tooling, workflows and common practices that let engineers benefit from coding agents, and assessing new models and products to decide what gets adopted. The engineer will also collaborate with the group responsible for Aperture by Tailscale, an AI gateway used internally and sold externally, and look for places where AI can accelerate other departments.
Responsibilities also include setting up guardrails, review routines and written guidance so AI-written code can be released safely, tracking how widely tools are adopted, and reporting their effect on speed and quality. The company does not impose a single tool and prefers that people reach for AI when it is appropriate.
Applicants should bring at least five years of professional engineering experience and daily, hands-on command of modern AI coding assistants such as Claude Code, Codex or Pi. Building internal utilities, handling uncertainty with self-set priorities, and thinking in products and systems are important. Assets include work in developer experience or platform teams, benchmarking language models and agents, proficiency in Go or Rust, and experience in security or reviewing code.
The job is remote-first. The posting cites a UK target base salary of £128,770 to £178,540 GBP, noting that individual offers can vary. AI-assisted tools help screen applicants, but people make every hiring decision.
Responsibilities
- Shape the internal AI enablement roadmap alongside engineering leaders
- Build tooling, workflows and practices that help engineers get value from coding agents
- Evaluate new models and tools and decide what to adopt
- Spot high-impact places to apply AI across engineering and other departments
- Set guardrails, review practices and documentation for AI-generated code
- Champion good habits across teams without imposing a single tool
- Track adoption and report AI tooling's impact to leadership
Requirements
- Five or more years of professional software engineering
- Daily, hands-on fluency with contemporary AI coding assistants
- Track record of creating in-house tools or automation for developers
- Strong written and spoken communication and the ability to win people over
- Balanced attitude toward AI, suited to a company without an AI mandate
- Comfort with uncertainty and setting one's own priorities
- Product and systems thinking
Qualifications
- Background in developer experience, platform work or internal tools
- Benchmarking LLMs or coding agents
- Systems programming in Go or Rust, alongside Python
- Security or code reviewing experience
- Developer relations or technical project management experience
Core Skills
Benefits
- Base salary, equity, and group health, vision and dental cover from day one
- Retirement contributions matched dollar for dollar up to 0.75% of eligible pay
- $1,500 USD per year for professional development
- Flexible paid time off and parental leave top-ups
- Home office support: laptop choice, monthly internet reimbursement and $500 USD for a workstation
- Annual company retreat and team off-sites
Frequently Asked Questions
Answers are based only on the employer’s listing; where it doesn’t say, neither do we.
Is this role remote?
Yes. The company describes itself as remote-first, and the posting does not require office attendance for this role.
What is the salary range?
The posting lists a UK target range of £128,770 to £178,540 GBP. Pay for a given hire can differ based on background and abilities.
Does Tailscale use AI in hiring?
Yes. AI-assisted tools help screen and assess applicants, but people make every hiring call, according to the posting.
How can I verify recruiter emails?
The posting says genuine messages from its talent team come only from its official company and recruiting-platform domains.
Sample Interview Questions
AI-generated questions tailored to this specific role — a preview of the full practice set.