Founding Machine Learning Engineer

The role

You will build ML systems that power autonomous underwriting decisions. You will own the full ML lifecycle from raw data to production and work with underwriters to advance autonomy levels.

What you will 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
• Develop confidence scoring and evaluation frameworks
• Work with large language models to build agentic workflows across the underwriting lifecycle
• Partner directly with underwriters to extract domain knowledge and validate outputs
• Contribute to the observability, monitoring, and guardrail infrastructure

Required qualifications

• 4+ years of industry experience building and shipping ML systems end-to-end
• Experience with model deployment platforms (e.g., AWS Sagemaker)
• Experience finetuning SLMs/LLMs
• 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
• Comfort with ambiguity, highly autonomous, and a bias toward building something real over architecting something perfect
• Excellent collaboration skills

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
• 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
• 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 health, dental, and vision
• Fertility benefits and family building support
• Flexible PTO
• Daily lunches, dinners, and snacks
• Professional Development
• Access to premium coaching, including leadership development
• Competitive 401(k) Plan
• Dog-friendly office

About the company

Shepherd rebuilds commercial insurance with software, data, AI, and deep underwriting expertise. The company is backed by Intact Private Capital, Costanoa Ventures, Spark Capital, Susa Ventures, and Y Combinator.