Founding Machine Learning Engineer

About the role

WHAT WE DO

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 industries and the progress they make possible.

OUR INVESTORS

In March 2026, Shepherd raised a $42M Series B https://www.linkedin.com/posts/justindlevine29_today-were-announcing-our-42m-series-b-activity-7442200922291630080-z1gw?rcm=ACoAAAkOMEwBRnAAXmdnQcaOJeioCu6VCqR6Gzc&utm_medium=member_desktop&utm_source=share — bringing total funding to over $60M — led by Intact Private Capital, the investment arm of one of the largest insurers in the world. Intact is not only our lead investor but also a carrier partner, a testament to the confidence the incumbent industry has in what we're building. Our investors:

- Intact Private Capital https://www.intactfc.com/about-us/intact-ventures, led our Series B round

- Costanoa Ventures https://costanoa.vc/, led our Series A round

- Spark Capital https://www.sparkcapital.com/, led our Seed round

- Susa Ventures https://www.susaventures.com/, lead our Pre-Seed round

- Y Combinator https://www.ycombinator.com/

- And several others

OUR TEAM

We're a team of technologists and insurance enthusiasts, bridging the two worlds together. Check out our About https://www.shepherdinsurance.com/about page to learn more.

THE MISSION: FULLY AUTONOMOUS UNDERWRITING

We think about underwriting autonomy the same way Waymo thinks about self-driving cars. Not as a binary switch, but as a graduated progression through defined capability levels. Today, Shepherd sits at the border of L1 for our first Operational Design Domain. You will build the ML systems that carry us from L1 to L3 and beyond. Every model you ship, every feedback loop you close, and every confidence threshold you calibrate is one more autonomous mile driven.

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

You will work directly with underwriters to deeply understand the domain, and translate that understanding into ML systems that get meaningfully better over time. You will own the full ML lifecycle – from data through to production – and be the connective tissue between the domain expertise that exists in the business and the systems we’re building to scale it.

WHAT YOU’LL DO

This is an end-to-end ML role. You will own the full lifecycle from raw data through to production systems, and work closely with underwriters, engineers, and product to advance FAU through its autonomy levels.

- 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)

HOW WE WORK

Shepherd runs on four values. Here's what each one means in this seat.

- Think big, build big. We exist to protect progress and the industries that rely on it. The work here is aimed at a system that runs on its own, and the roadmap gets sequenced backward from that rather than forward from what's easy.

- Win together. We rise as one. We support each other, raise the bar, and celebrate collective success. As the first PM you set a standard the rest of the team inherits, and the milestones belong to the team rather than to product.

- Cross the aisle. Collaboration wins. We listen deeply, work across boundaries, and prioritize shared success over individual lanes. The best product calls here come from engineers who've sat with underwriters and underwriters who understand where the model breaks, and much of this job is listening closely enough on both sides to make that happen.

- Go get it. We act with urgency, move with confidence, take smart risks, and push forward with intention. Nobody hands you the roadmap, the data, or the meeting invite. You pull the failing runs, book the time with the underwriters, and decide what matters.

BENEFITS

🏥 Premium Healthcare
100% contribution to top-tier health, dental, and vision

🥕 Fertility benefits and family building support

🏖️ Unlimited PTO
Flexibility to take the time off, recharge, and perform

🥗 Daily lunches, dinners, and snacks
We work together, and enjoy meals together too

🖥️ 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
Plenty of dogs to play with and make friends with in the SF office