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Senior/Staff Software Engineer - Conversational AI

ExpressVPN

3.6
1 review
ExpressVPN
Job Type   /   Job Level
Full-time   /   Senior Executive
Company Location
Singapore
We're building production conversational AI — LLM agents that hold real conversations at scale, answer from a grounded knowledge base, and know their limits. We're looking for a hands-on Lead AI Engineer to own it end to end: the AI behavior, the infrastructure, and the full stack around it.

We're a small, focused team tackling a big problem — making AI that's accurate, grounded, and trustworthy in production. That means high ownership, fast decisions, and direct impact: what you build ships and runs live.

This is a builder-leader role. You write code, make the architecture calls, and set the technical direction for the team.

What You'll Do

  • Own the AI system — LLM agents, retrieval-augmented generation (RAG), and guardrails. Drive answer quality, retrieval relevance, and safe behavior.
  • Debug and improve AI behavior — diagnose why a model hallucinated, mis-routed, or responded incorrectly, and design evaluations (LLM-as-judge and others) to measure and prevent it. Turn vague "it answered badly" reports into measured fixes.
  • Lead platform engineering — design and ship the services, data pipelines, and tooling that let the product scale reliably.
  • Own infrastructure as code — Terraform across multiple environments, CI/CD, and a server-less cloud footprint.
  • Build full-stack — backend services, an internal web app, and data-processing pipelines.
  • Own security and data protection — treat it as first-class: data isolation, least-privilege access, encryption, careful handling of credentials and sensitive user data. Security is a core requirement of everything we ship, not an afterthought.
  • Set technical direction — review designs and code, define quality bars, and keep production healthy.

Must have

  • You've shipped an LLM application to production — agents and/or retrieval-augmented generation (RAG), with guardrails and a vector/embeddings layer. Not just prototypes.
  • Strong prompt engineering and AI debugging — you can reason about model behavior and build evaluations to measure it.
  • Terraform / infrastructure as code and solid AWS depth (serverless compute, NoSQL, event-driven flows, IAM).
  • Full-stack engineering — TypeScript/Node, a modern web framework (React/Next.js), and Python for data work.
  • Strong security and data-protection fundamentals — you build systems that handle sensitive user data safely: data isolation, least-privilege access, encryption, and secrets management.
  • Ownership and technical leadership — able to lead a project and keep a production system reliable.

Nice to have

  • Experience with Amazon Bedrock (agents, knowledge bases, guardrails) — a strong advantage.
  • SaaS / multi-tenant platform design.
  • Production observability and cost optimization for AI workloads.

What Success Looks Like

  • The AI answers more questions correctly and grounded, and stays within its limits — measured, not guessed.
  • The platform scales smoothly, with safe and repeatable infrastructure changes.

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