ML/AI Engineer, Applied AI
About this role
We're looking for an ML/AI Engineer, Applied AI to build the AI systems layer behind Drawbridge's process intelligence platform.
This is a full-time role for a senior applied AI engineer who cares about making AI behavior measurable, reliable, safe, and useful in production. We build production AI systems on top of hosted frontier models from providers like OpenAI, Anthropic, Gemini, and Cohere.
You will own the systems that turn messy enterprise data into structured process intelligence: retrieval, context construction, model/provider selection, structured extraction, evals, orchestration, quality loops, and monitoring.
Impact: You'll directly improve the quality, reliability, and usefulness of Drawbridge's AI outputs.
Applied AI ownership: You'll build and own the production systems around LLM APIs.
Evaluation discipline: You'll create the datasets, tests, and quality gates that help us know when the system is improving or regressing.
Product partnership: You'll work closely with backend, product, and forward deployed engineering to solve real customer workflow problems.
Technical leverage: Your work will shape how Drawbridge chooses models, constructs context, evaluates outputs, manages cost/latency, and safely ships AI behavior.
What we're looking for
Must-haves
4-6+ years building production software, ML systems, or applied AI systems
Evaluation mindset: You know how to design tests, compare outputs, build datasets, measure quality, and prevent regressions
Data quality judgment: You understand that AI quality depends on source data, context, labels, edge cases, and feedback loops
Production reliability: You care about latency, cost, observability, retries, failure modes, and making systems debuggable
Systems thinking: You can reason about pipelines end-to-end, from raw customer data to generated outputs and user-facing product behavior
Comfort with ambiguity: You can turn a fuzzy product goal into experiments, implementation, measurement, and shipped improvements
Practical LLM experience: You've built with hosted LLM APIs, including prompting, structured outputs, embeddings, retrieval, tool use, or workflow orchestration
Strong Python skills: You can build reliable services, data pipelines, eval workflows, and AI tooling in production-quality Python
Strongly preferred
RAG and retrieval: Embeddings, vector search, hybrid search, chunking, ranking, reranking, context assembly, or knowledge-base systems
LLM evals: Golden datasets, LLM-as-judge, human review workflows, regression testing, launch gates, offline and online evaluation
Agent/tool orchestration: Multi-step AI workflows, tool calling, structured outputs, planner/executor patterns, or agent reliability work
Prompt and context optimization: Improving output quality through prompt design, schema design, context selection, and model/provider comparison
Safety and guardrails: Reducing hallucinations, enforcing constraints, handling sensitive data, or designing verification and fallback paths
Cost and latency tradeoffs: Practical experience balancing model quality, speed, reliability, and spend
Nice to have
NLP or document understanding: Extraction, classification, summarization, entity resolution, semantic search, or long-context workflows
Process mining, task mining, or enterprise workflow experience
Multimodal inputs: Experience with documents, screenshots, video, transcripts, or mixed enterprise data sources
Go or backend service experience
Customer-facing AI product experience
AI-assisted development: You already use tools like Claude Code, Cursor, Codex, Copilot, or similar to accelerate your work
Our tech stack
Go, Python, PostgreSQL, Redis/Valkey, React 19 + TypeScript, GCP, Terraform, Docker, Datadog, GitHub
AI systems: hosted LLM APIs (OpenAI, Anthropic, Gemini, Cohere), embeddings and retrieval, structured extraction, agent/tool-calling workflows, eval pipelines, and AI observability
Company at a glance
Drawbridge builds a platform combining process intelligence and agentic AI to automate enterprise operations by reverse-engineering workflows into executable specifications for AI systems.
What happens next
Skip the application pile. I get you in front of the people who decide.
Confirm the fit
A few questions to make sure this role is the right shape for you. Two minutes.
I pitch you to the company
I write the intro, send it to the founder, and handle the back-and-forth.
A meeting lands on your calendar
When the company wants to meet, I get the call on your calendar. You just show up.
Culture & values
5-days-in-office culture in San Francisco and New York City
High ownership with architectural decision-making authority
Direct founder collaboration with significant technical decision-making authority
Customer obsession with engineers expected to jump on calls with customers and iterate based on direct feedback
AI-native development culture using AI-assisted tools like Claude Code, Cursor, and Codex
Team values curiosity, pragmatism, and a builder mentality
Young, clean codebase where architectural decisions set patterns for the platform
High velocity operating environment
Engineers expected to build exactly what provides the best customer experience
Know someone who'd be great for this?
