What We Do

Commercial insurance still runs on processes built decades ago. Underwriting is slow, and pricing leans on broad averages instead of the specifics of each risk. Technology can change how commercial risk is priced and managed, as long as it's paired with real underwriting expertise. The companies that get this right will shape the next era of the industry, and Shepherd intends to lead it.

Shepherd is a Managing General Underwriter (MGU) building the fastest and smartest AI-native commercial risk platform in the industry, where underwriters, data, and automation work together. The result is faster decisions for our broker partners and pricing that reflects the actual risk.

We started where the gap is widest: construction and energy, two of the most complex and highest-hazard segments in commercial insurance. Today we write Primary and Excess Casualty, Builder’s Risk, and Workers' Compensation distributed through a nationwide network of retail brokers. Our mission is to make risk frictionless for the builders and operators shaping the physical world, from concept through construction and into decades of operation.

Our Investors

Shepherd has raised over $67M, including a $42M Series B led by Intact Private Capital. Intact also partners with Shepherd to provide capacity across its insurance products. Shepherd is also backed by leading institutional investors, including Costanoa Ventures, Spark Capital, Susa Ventures, and Y Combinator.

The Role

We are seeking a detail-oriented and analytical Actuarial Analyst to join our actuarial team supporting multiple commercial lines of business, including General Liability, Workers' Compensation, Commercial Property, and Excess Casualty. This role is perfect for someone who thrives on executing rigorous insurance analysis, collaborating cross-functionally, and delivering precise, actionable insights that drive competitive advantage.

As an Actuarial Data Analyst, you will be the bridge between market intelligence, regulatory requirements, and data-driven product decisions. You will be joining a small team of actuaries playing a critical role in ensuring our products remain competitive while maintaining compliance across all jurisdictions where we operate. The actuarial team works in close partnership with underwriters and software engineers, translating actuarial insights into the technology and decisions that power a modern insurance platform.

Key Responsibilities

Ratemaking & Competitive Intelligence (50%)

• Assist in the development, pricing, and implementation of rating plans for filing with state Departments of Insurance

• Support the Compliance team in the preparation, documentation, and submission of rate and form filings

• Conduct comprehensive competitor analysis of rate and form filings across all commercial lines, utilizing SERFF, S&P Capital IQ Pro, and other regulatory databases to identify market trends and competitive positioning

• Analyze filings, rate manuals, underwriting guidelines, and coverage forms from industry resources including ISO manuals and NCCI data to develop detailed benchmarks and strategic recommendations

• Research and draft comprehensive responses to rate-related objections, ensuring actuarial justification is provided

Actuarial Reporting & Portfolio Monitoring (25%)

• Perform loss ratio analysis by line of business, territory, and risk characteristics to identify profitable segments and areas of concern

• Develop and maintain reporting requirements, including bordereaux and portfolio reporting, coordinating with internal teams and external partners on data accuracy and timely delivery

• Support workers’ compensation statistical reporting obligations, including WCSTAT and WCPOLS

Data Analytics (25%)

• Write SQL queries to extract and analyze data related to premium volumes, loss ratios, exposure metrics, and rate change impacts from internal PostgreSQL databases

• Create interactive BI dashboards using Metabase or similar platforms to track key product performance metrics

• Support data transformation processes using dbt for analytics and reporting workflows

Required Qualifications

Experience & Education

• 2-5 years of experience in commercial P&C insurance product analysis, actuarial, or competitive analysis functions

• Bachelor’s degree in Mathematics, Statistics, Economics, Finance, or related analytical field

• Demonstrated experience with commercial insurance products and insurance data analytics

• Actuarial exams such as P, FM, MAS-I, MAS-II, 5 (preferred but not required)

Technical Skills

• Advanced SQL proficiency for data extraction, manipulation, and analysis from PostgreSQL databases

• SERFF system knowledge including navigation, filing preparation, and objection response processes

• Advanced spreadsheet modeling skills for financial analysis and data manipulation

• Experience with industry databases and tools including ISO manuals, NCCI data, and regulatory research platforms

• Python experience for advanced analytics (preferred but not required)

Insurance Knowledge

• Understanding of commercial insurance products including rating methodologies and underwriting guidelines

• Knowledge of state insurance filings process

• Understanding of ISO forms, NCCI guidelines, and industry standard practices

• Understanding of actuarial concepts including loss development, rate adequacy, and predictive modeling principles

Core Competencies

• Strong analytical and critical thinking skills with ability to translate data into insights and recommendations

• Exceptional attention to detail and accuracy, especially for time-sensitive regulatory deliverables

• Clear communication skills for both technical and non-technical audiences

• Cross-functional collaboration experience working with actuarial, underwriting, compliance, and product management teams

What We Offer

• Competitive salary ranging from $110,000 - $140,000 based on experience and qualifications

• Equity participation with significant upside potential in our growing organization

• Comprehensive benefits package including health, dental, vision, and 401(k) with company match

• Professional development opportunities including conference attendance and certification support

• Collaborative startup environment with opportunities for rapid career growth and expanded responsibilities

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. Come set a standard the rest of the team inherits.

• 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 Healthcare100% contribution to top-tier health, dental, and vision

Fertility benefits and family building support

️ Unlimited PTOFlexibility to take the time off, recharge, and perform

Daily lunches, dinners, and snacksWe work together, and enjoy meals together too

️ SF, NYC, Dallas-Fort Worth, Chicago and LA Offices

Professional DevelopmentAccess to premium coaching, including leadership development

Competitive401(k) Plan

Dog-friendly officePlenty of dogs to play with and make friends with in the SF office