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Two DotsTwo DotsSan Francisco, CA

Member of the Technical Staff - Chatbot Engineer

As a Member of the Technical Staff, you will build consumer-facing chat agents that serve as the frontend to complex workflows. This role requires strong Python ability, user empathy, and a metrics-driven approach to understanding and improving chat agent quality.

175k – 275k
On-siteML Engineering

About the role

The Role

Chat agents are becoming the primary interaction surface of the future. We are looking for a software engineer who can build consumer-facing chat agents that serve as the frontend to complex workflows. This role requires a rare combination of user empathy, strong written English, strong Python ability, and a metrics-driven mentality. You should be comfortable using SQL or BigQuery to understand quality, but also know when to roll up your sleeves and do manual QA rather than treating every product problem like back-propagation. You are essentially a future version of a UX Engineer, but for conversational natural language experiences instead of buttons and forms.

What You'll Work On

  • Consumer-facing chatbots that serve as the frontend to complex workflows
  • Bridging internal workflow APIs and domain object code with the real-world call patterns of AI agents
  • Making smaller models perform like larger models
  • Designing creative ways to automate product judgment, such as using chatbots to roleplay users instead of relying only on manual QA or fixed test cases
  • Working closely with design and product to balance look and feel, interaction quality, and business objectives

What We're Looking For

  • You understand context management deeply. You know the difference between a workflow that makes LLM calls and a true agent loop with tool calling. You know how to start with a smart model and move to cheaper, faster ones without relying on prompt hacks, “CRITICAL:” advisories, or endless lists of dos and don’ts.
  • You understand what belongs in tools and APIs versus what belongs in natural language. Designing that boundary should be a fixation for you.
  • You also understand what is structural and what is in the domain of tone, framing, or model “dark magic.” You care about the headspace the model is operating in, the quality of the user experience, and whether the product actually works for confused real people.
  • Despite working on agents, you are not in “Gas Town.” You do not believe every problem requires a meta-harness, and you do not outsource your judgment to chatbots. You know when to escalate to MLEs if a problem likely requires fine-tuning or more advanced methods.
  • You care deeply about user outcomes. You measure how your experiments are doing, proactively solve quality problems, and have the frustration tolerance required for ambiguous chatbot engineering.

Technical Fit

  • Python is preferred. TypeScript or other strong software engineering backgrounds are also welcome.
  • You should be a strong enough programmer to build reliable systems manually, not just prompt your way through implementation.

Compensation

The higher end of the band is for rare candidates with a combination of strong engineering, product judgment, and conversational design experience. The lower end is for solid mid-career software engineers with meaningful professional or personal experience building chat agents that interact with real systems.

Skills

PythonSQLBigQueryTypeScriptLLMsAPI DesignChatbot DevelopmentNatural Language ProcessingUser EmpathyMetrics-Driven Development

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