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 — 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, led our Series B round
Costanoa Ventures, led our Series A round
Spark Capital, led our Seed round
Susa Ventures, lead our Pre-Seed round
Y Combinator
And several others

Our Team

We're a team of technologists and insurance enthusiasts, bridging the two worlds together. Check out our About page to learn more.

About the Role

Shepherd is building the data infrastructure and predictive models that power modern commercial insurance. As an Actuarial Data Science Lead on the Actuarial & Predictive Analytics team, you will own the development of pricing models starting with commercial auto, one of our highest-volume and most data-rich lines. You'll directly shape the quality of the book we write and the products we bring to market.

This is a high-impact, individual-contributor role for someone who thrives at the intersection of statistical rigor and shipping real products. You will work closely with actuaries, underwriters, and engineers to turn data into decisions.

What You'll Do

Own commercial auto pricing models end-to-end from feature development through deployment and iterate on them as the book grows and new data sources come online
Build and deploy predictive models build and deploy loss cost models that set pricing for Shepherd's commercial auto book
Design and maintain feature pipelines that transform raw submission, claims, and third-party data into model-ready inputs
Collaborate with actuaries and underwriters to translate domain expertise into model features and validate outputs against real-world outcomes
Develop model monitoring frameworks to track drift, performance degradation, and calibration over time
Run experiments and back-tests to quantify model impact on loss ratios, pricing accuracy, and portfolio quality
Communicate findings clearly to technical and non-technical stakeholders through concise documentation and presentations

What We're Looking For

Must-Haves

7+ years of professional experience building and deploying personal auto or commercial lines predictive pricing models in production
Familiarity with actuarial concepts (loss development, exposure rating, credibility)
Strong foundation in statistics: GLMs, GBDTs, time series analysis, heavy tail distributions, and Bayesian methods
Proficiency in Python and SQL
ACAS/FCAS actuarial designation
Experience with feature engineering on messy, real-world, small data
Ability to reason from first principles and communicate results crisply to non-technical audiences
AI-native mindset: you already use LLMs and AI tools to accelerate your own work
Experience managing a small team or project

Nice-to-Haves

Experience in insurance, insurtech, fintech, or other regulated industries
Exposure to telematics pricing models
Experience with NLP/document extraction from unstructured insurance submissions
Prior work with model deployment infrastructure (AWS)

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

Actuarial Data Science Lead