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ShepherdShepherd

Founding Machine Learning Engineer

Builds end-to-end ML systems for autonomous insurance underwriting, finetuning LLMs, closing feedback loops with underwriter data, and deploying production models. Requires 4+ years ML experience, Python proficiency, and production LLM expertise.

About the job

What You’ll Do

  • Design, build, and ship ML systems that power autonomous underwriting decisions in production
  • Build and close the feedback loops that turn human underwriter behavior into training signal and compounding model improvement
  • Develop confidence scoring and evaluation frameworks that define when the system is ready to take on more autonomy and when to step back
  • Work with large language models to build reliable, auditable, and improvable agentic workflows across the underwriting lifecycle
  • Partner directly with underwriters to extract domain knowledge, validate outputs, and earn the trust required to expand the system’s operating domain
  • Contribute to the observability, monitoring, and guardrail infrastructure that keeps AI underwriting safe as autonomy scales

Who You Are

Required

  • 4+ years of industry experience building and shipping ML systems end-to-end, from raw data to production models, including experience with model deployment platforms (e.g., AWS Sagemaker)
  • Experience finetuning SLMs/LLMs, with a preference for experience using techniques like RLHF, DPO, or LoRA
  • Deep proficiency in Python and modern ML frameworks (PyTorch, HuggingFace, Tensorflow, OpenAI Gym/Gymnasium or similar)
  • Experience with LLMs in production: prompt engineering, structured outputs, tool use, evaluation, and cost/latency tradeoffs
  • Experience building reliable models with limited labeled data, including synthetic data generation, data augmentation, or similar techniques
  • Strong evaluation instincts: you know how to define what ‘better’ means before you build, not after
  • Comfort with ambiguity, highly autonomous, and a bias toward building something real over architecting something perfect
  • Excellent collaboration skills. You will spend significant time with non-technical underwriters and need to earn their trust

Nice to Have

  • Familiarity with document parsing, information extraction, or NLP on unstructured business documents
  • Background in insurance, finance, or other high-stakes structured domains where model errors have real consequences
  • Experience with agentic frameworks or multi-step LLM orchestration (LangChain, LangGraph, or custom)
  • Confidence calibration experience: isotonic regression, Platt scaling, or similar techniques
  • TypeScript proficiency. Our platform is TypeScript-heavy and cross-functional contribution is valued
  • Familiarity with data pipelines: SQL, dbt, Spark, or equivalent
  • MS or PhD in a quantitative field (ML/AI, Statistics, Math, Physics)

Benefits

  • Premium Healthcare: 100% contribution to top-tier health, dental, and vision
  • Fertility benefits and family building support
  • Unlimited PTO
  • Daily lunches, dinners, and snacks
  • SF, NYC, Dallas-Fort Worth, Chicago and LA Offices
  • Professional Development: Access to premium coaching, including leadership development
  • Competitive 401(k) Plan
  • Dog-friendly office

Skills

Python, PyTorch, Huggingface, TensorFlow, Aws Sagemaker, LLMs, RLHF, Dpo, Lora, Prompt Engineering, NLP, LangChain, LangGraph, SQL, dbt

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