Two Dots

Two Dots

Member of the Technical Staff - Chatbot Engineer

San Francisco HQ · Staff+

Sponsorship not specifiedDetected 64 days ago
TypeScriptPythonSQLBigQueryMachine LearningLLMsAgentic AILogistics

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odds of building a lasting career here

16Unrated
Cap-exempt (no lottery)0
Sponsors this role0
Entry-level history0
PERM / green-card track0
Lottery odds40
Fits your clock70

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About the role

  • Chat agents are becoming the primary interaction surface of the future.
  • It sounds easy to make a good chatbot, but many systems fail because they misunderstand users, overfit prompts, hide structural problems, or turn complex workflows into brittle demos.
  • This role requires a rare combination of user empathy, strong written English, strong Python ability, and a metrics-driven mentality.

Responsibilities

  • Working closely with design and product to balance look and feel, interaction quality, and business objectives
  • 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.
  • Prompt Engineering / Agent Design Screen: We discuss how you approach agent quality, context management, tool use, prompt structure, and evaluation.
  • Product / Design Interview: We evaluate how you diagnose and improve conversational product experiences, including user-facing language, subjective quality, and measurement.
  • Prompt Engineering / Agent Design Screen:
  • Product / Design Interview:

Requirements

  • 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.
  • 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 measure how your experiments are doing, proactively solve quality problems, and have the frustration tolerance required for ambiguous chatbot engineering.
  • That combination of specific consumer fintech experience and knowledge of how sophisticated ML products succeed in production made big enterprise deals work from day 1.

Nice to have

  • Python is preferred.

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.

Company info

  • Henson (CEO) started his career selling FX derivatives to hedge funds at Goldman, then worked at a real estate tech startup for several years leading sales.
  • This enables him to engage with the largest institutional property managers and real estate investors in the country and create value through those relationships.
  • Max (CTO) started out as a software engineer at Blend, a mortgage application company that went public, and went on to work on the search team at Google.
  • We met in middle school and created a media website together where people could watch and post their flash games and animations.
  • We learned to code, source talent, and forge partnerships - and had 500 active users.
  • Although a tragic addiction to World of Warcraft interrupted work on the website, we got back together to start Two Dots.
  • Other team members include: Meta ML alumnus with decades of experience, a 21 year old UMich grad who was a top 2,000 LoL player (he is no longer playing the game, thank god), and a former agave farmer who started a shipping and logistics company while at Stanford.
  • Technical Fit
  • 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
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This listing is sourced directly from Two Dots's careers page and normalized into a canonical job model.