New opportunity

Member of the Technical Staff — AI/ML

Stuut · San Francisco; New York City, United States

About this role

Stuut is hiring a hands-on AI/ML engineer to turn AI research into production-grade systems for B2B financial operations. The role focuses on agentic applications that improve workflows such as invoice matching, payment reconciliation and financial document processing.

Responsibilities

  • Build production-ready, tool-using LLM agents that surface insights, recommend next steps and execute approved tasks. Develop scalable AI features that integrate with Stuut’s platform.
  • Apply and optimize LLMs and RAG for financial workflows, fine-tuning on proprietary data when useful. Build reliable, maintainable and cost-efficient pipelines from ingestion through inference, including model routing.
  • Establish golden datasets, agent tracing, regression testing on pull requests and A/B tests. Instrument features, monitor outcomes and iterate to catch regressions and improve performance.
  • Work with Product, Engineering, Data and customers to translate business needs into technical solutions.

Qualifications

  • At least 5 years of AI/ML experience and a record of shipping AI/ML products that solve business problems, including agentic products in production. Understand agent failure modes involving tool use, planning, state, recovery and human oversight.
  • Experience integrating and fine-tuning LLMs, building RAG systems for document- or data-intensive workflows, and training and deploying classical ML models such as risk scoring, forecasting or ranking systems. This includes feature engineering, model selection, evaluation and calibration.
  • Knowledge of offline and online evaluation, statistical significance, evaluations in CI, LLM tracing and observability, and MLOps practices including deployment, monitoring, A/B testing, model and prompt versioning, and feature stores. Fluency in Python and AI/ML tools such as PyTorch, Transformers, scikit-learn, XGBoost, vLLM, LangChain or LlamaIndex is sought.

Preferred

Experience routing models across providers or working in fintech, B2B SaaS, or accounts receivable/accounts payable.

The full-time role is on-site in San Francisco or New York City. Estimated salary is $220K–$350K per year, with equity. For U.S.-based full-time employees, listed benefits include medical, dental and vision coverage, a 401(k) match, flexible PTO and parental leave.

For full details about this role, click “Apply on company site” to view the employer’s original posting.

Skills for this role

AI agentsLarge language modelsRetrieval-augmented generationLLM fine-tuningMachine learningPythonPyTorchTransformersscikit-learnXGBoostvLLMLangChainLlamaIndexLangSmithBraintrustArizeModel routingFeature engineeringModel evaluationModel calibrationGolden datasetsAgent tracingA/B testingMLOpsFeature storesPrompt versioningHuman-in-the-loop systemsFinancial document processing

Your skill match

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Get interview-ready for this role

A focused preparation guide, built around this job’s responsibilities and requirements.

✦ AI-generated guide
Preparation suggestions, not the employer’s actual interview questions. Always check the original posting for current requirements.
01

Understand the role

What matters most

  • Production-grade financial agents

    Build tool-using LLM agents that surface insights, recommend next steps and execute approved tasks. The posting emphasizes deployed systems and understanding failures in tool use, planning, state, recovery and human oversight.

  • Useful workflow improvements

    Refine invoice matching, payment reconciliation and financial document processing as features integrated with Stuut’s platform, rather than standalone prototypes.

  • Practical model and pipeline choices

    Apply LLMs and RAG to financial workflows, fine-tune on proprietary data when useful, and build reliable, maintainable ingestion-to-inference pipelines with cost-conscious model routing. The role also calls for experience deploying classical ML models.

  • Evaluation and continuous improvement

    Establish golden datasets, agent tracing, regression tests on pull requests and A/B tests. Instrument deployed features, monitor outcomes and iterate to catch silent regressions.

  • Translate needs into customer impact

    Work with Product, Engineering, Data and customers to turn financial-operations needs into technical solutions with measurable business value.

Likely challenges to think through

  • Balancing agent action with oversight

    Likely preparation challenge, not a confirmed problem: executing approved financial tasks can be more consequential than recommending them. Prepare to explain how an agent would track state, detect tool or planning failures, recover safely and involve a human when needed.

  • Choosing capability without unnecessary cost

    Likely preparation challenge: better model output may increase inference cost or pipeline complexity. Prepare a decision framework for when to use RAG, fine-tuning, model routing or classical ML, and how to compare quality, reliability, cost and maintainability.

  • Connecting test results to real outcomes

    Likely preparation challenge: offline evaluations may miss workflow edge cases or fail to predict customer impact. Prepare to describe how golden datasets, traces and pull-request regressions would complement online monitoring and statistically sound A/B tests.

03

Practice your answers

Technical practice

How would you design a tool-using LLM agent that recommends next steps but executes only approved financial tasks?

What to coverPreparation suggestion: Explain how the agent would distinguish advice from action, check approval before tool calls, and record what it did. Discuss the trade-off between useful automation and human oversight.

How would you diagnose and recover from an agent that loses state or takes the wrong step in a financial workflow?

What to coverPreparation suggestion: Walk through tool-use and planning failures, how traces would expose the point of failure, and when to pause for human review. Explain how you would resume or stop work without silently repeating an action.

How would you improve invoice matching or payment reconciliation when the available financial documents disagree?

What to coverPreparation suggestion: Describe how you would ingest and compare records, handle ambiguous matches, and decide when to escalate rather than automate. Explain how you would measure matching quality and downstream workflow impact.

How would you build and evaluate RAG for document-intensive financial operations?

What to coverPreparation suggestion: Cover document ingestion, retrieval quality, grounding of generated answers, and handling missing or conflicting evidence. Distinguish retrieval errors from generation errors when diagnosing poor results.

When would fine-tuning an LLM on proprietary data be preferable to improving retrieval or prompts?

What to coverPreparation suggestion: Define the failure you are trying to fix and compare expected gains against data, maintenance, and inference costs. Explain what evaluation would show that fine-tuning moved the needle.

How would you design a reliable, cost-efficient ingestion-to-inference pipeline with model routing?

What to coverPreparation suggestion: Explain how you would choose routes based on task quality, latency, and cost, and how you would handle a model or provider failure. Describe what you would measure to tell whether routing improves the complete workflow.

How would you develop a classical ML model for risk scoring, forecasting, or ranking in this domain?

What to coverPreparation suggestion: Walk through feature engineering, model selection, evaluation, and calibration using one of the model types named in the posting. Explain how you would check whether offline results remain useful after deployment.

How would you use golden datasets and pull-request regression tests for an agentic feature?

What to coverPreparation suggestion: Describe how you would choose representative cases and score both task outcomes and unsafe or incorrect actions. Explain which changes would block a release and how you would investigate a regression.

How would you run an A/B test of a new AI feature and judge whether it improved outcomes?

What to coverPreparation suggestion: Define a customer-relevant outcome alongside quality and reliability guardrails. Discuss statistical significance and why an apparent online improvement might conflict with offline evaluation.

What would you instrument and version to keep a deployed AI feature improving?

What to coverPreparation suggestion: Discuss agent tracing, outcome monitoring, and model and prompt versioning so a change can be tied to its effects. Explain how deployment and rollback decisions would use that evidence, including when feature-store inputs matter.

Behavioural practice

Tell me about a time you translated an ambiguous customer or business need into an AI solution.

What to coverPreparation suggestion: Use a real situation to show how you worked with product, engineering, data, or customers to clarify the need and choose a technical approach. State your actions and the result, including how you determined whether the solution addressed the need.

Tell me about an AI/ML product you helped take from prototype to production.

What to coverPreparation suggestion: Describe the situation, your specific engineering decisions, and how you handled reliability or maintainability rather than stopping at a demo. Give the observed result and explain what evidence connected the product to a business outcome.

Tell me about a production AI failure or silent regression you investigated.

What to coverPreparation suggestion: Set out the situation, the signals or traces you used, and the actions you took to contain and diagnose the issue. Close with the result and any evaluation or monitoring change that followed.

Tell me about a time you had to balance automation against human oversight.

What to coverPreparation suggestion: Give a real situation involving a consequential action or uncertain model output, then explain your decision and how you aligned stakeholders. Describe the result without claiming that oversight eliminated all risk.

Tell me about a time you decided whether new AI research was ready for a practical product use case.

What to coverPreparation suggestion: Describe the business problem, how you tested the approach against an alternative, and the trade-offs you considered. State what you chose to do and what the resulting evidence showed.

02

Sharpen your knowledge

Topics to prepare

  • Agent reliability and human oversight

    The posting emphasizes tool use, planning, state, recovery and human-in-the-loop failure modes. Revision exercise: walk through an invoice-matching agent that recommends an action but may execute it only after approval; identify how it handles a failed tool call, stale state and an ambiguous match.

  • RAG versus LLM fine-tuning

    Stuut calls for RAG in document- or data-intensive financial workflows and fine-tuning proprietary data where useful. Revision exercise: compare retrieval, fine-tuning and a simpler baseline for answering questions from financial documents; state what evidence would justify each choice.

  • Classical ML model decisions

    The posting explicitly names deployed risk-scoring, forecasting or ranking models, including feature engineering, selection, evaluation and calibration. Revision exercise: outline a ranking model for payment follow-up, then explain how you would check both ranking quality and score calibration.

  • Offline and online evaluation

    Golden datasets, evaluations in CI, A/B testing and statistical significance are explicit priorities. Revision exercise: design an offline regression check and an online comparison for invoice matching; define what would count as a meaningful improvement or a silent regression.

  • Production pipeline tradeoffs

    The role covers ingestion through inference, reliability, maintainability, cost efficiency and model routing. Revision exercise: sketch that pipeline for financial document processing and explain where a routing decision could reduce cost without compromising an evaluation target.

  • Receivables workflow context

    The role names invoice matching and payment reconciliation within broader B2B order-to-cash workflows; AR/AP experience is a bonus, not a stated requirement. As preparation, trace a hypothetical invoice and payment through matching, reconciliation and exception handling, marking where an AI recommendation would need review.

Skills to revise

  • Implement an approval-gated agent

    The posting calls for production-ready, tool-using LLM agents that execute approved tasks. Practice in Python with a small synthetic workflow: return a proposed reconciliation action, require explicit approval before execution, and test failed calls and recovery. This is a suggested exercise, not a specified employer assignment.

  • Build and assess a document RAG pipeline

    Stuut seeks LLM integration and RAG for financial workflows. As practice, ingest sample financial documents, retrieve evidence for an invoice question, and inspect incorrect or unsupported answers. Use sample data rather than assuming access to Stuut’s proprietary data.

  • Train and calibrate a classical model

    The posting asks for hands-on feature engineering, model evaluation and calibration. Practice with synthetic tabular payment data in Python and a listed tool such as scikit-learn: train a risk or ranking baseline, check held-out performance, and examine calibration.

  • Create regression data and traces

    Golden datasets, agent tracing and regression-on-PR are named responsibilities. Practice assembling a small labeled set of matching cases, recording each agent’s tool calls and outcomes, and writing a test that fails when a known case regresses; the exercise is illustrative, not a claim about Stuut’s test setup.

  • Instrument a controlled rollout

    The posting calls for monitoring outcomes, A/B testing and model and prompt versioning. Practice defining version identifiers, outcome metrics and a comparison plan for two invoice-matching variants, including how you would detect degradation after deployment.

04

Your preparation checklist

  • Map the financial workflow

    Sketch how invoice matching or payment reconciliation fits into Stuut’s order-to-cash work. Use the posting’s scope as context; mark any assumptions you would need to validate.

  • Prepare a production project walkthrough

    If you have a relevant shipped AI/ML product, bring a concise account of the business problem, your decisions, deployment, measured outcomes and lessons learned. Distinguish production evidence from prototype work.

  • Practice a tool-using agent design

    As an interview exercise, diagram an agent that recommends a reconciliation step and executes it only after approval. Explain tool-use, planning and state failures, recovery paths and human oversight.

  • Compare LLM pipeline choices

    Draft an ingestion-to-inference design for financial documents. Show where RAG, fine-tuning or model routing might help, and how you would test quality, reliability and cost before choosing.

  • Assemble classical ML evidence

    If applicable, prepare one risk-scoring, forecasting or ranking example covering feature engineering, model selection, evaluation, calibration and deployment. The posting seeks deployed classical ML as well as LLM experience.

  • Build an evaluation and monitoring plan

    Outline a golden dataset, agent traces, pull-request regression checks and an online A/B test. Specify failure metrics, a statistical decision rule, and how model and prompt versions would be monitored.

  • Write collaboration questions

    Prepare questions for Product, Engineering, Data and customer-facing partners about workflow pain points, approval boundaries, available evaluation data and how they measure customer impact.

AI-generated from the job information · Prepared Sep 30, 2026 (UTC)Useful preparation, not a guarantee of eligibility or an offer.

Availability last checked: Nov 4, 2026. Status can change after a check; confirm on the employer’s website. Report an issue · Our checking policy

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