The all-in-one learning co-pilot. Backed by Y Combinator.
About the role
You will be Shepherd’s first Machine Learning Engineer, embedded in the Fully Autonomous Underwriting (FAU) team. This is a high-ownership, high-ambiguity role. There is no existing ML platform to inherit, no established model registry to maintain. You will build those things. You have the opportunity to define the ML function from the ground up at a company building something genuinely new in a large, underserved market
What they're looking for
- 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
More about this role
Yesterday's insurance wasn't built for today's risk. We see it in the data and we feel it in the field. Emerging technology can reinvent how risk is priced and managed, faster and smarter, anchored in proven expertise. First-movers will define the next era of commercial risk management, and Shepherd is building it.
Shepherd is a technology-driven Managing General Underwriter (MGU) transforming commercial Property & Casualty insurance for high-hazard industries. Our mission is to make risk frictionless for the builders and operators shaping the physical world, protecting progress from concept through construction and into decades of operation.
We're building the fastest, smartest commercial risk platform, where underwriting expertise, data, and automation work together to deliver:
Faster decisions
Smarter, more accurate pricing
Better risk outcomes
With Shepherd, safety, speed, and quality no longer trade off against one another. They compound. We're not just modernizing insurance products. We're building the risk infrastructure for the next generation of financial services, where technology, underwriting, and partnerships operate in harmony to support the world's most important...
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