GTM Analytics & Strategy

What We DoShepherd 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 decisionsSmarter, more accurate pricingBetter risk outcomesWith 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 InvestorsTo date, Shepherd has raised over $20M from leading investors, including:Spark CapitalCostanoa VenturesY CombinatorSusa VenturesIntact VenturesAnd several othersOur TeamWe're a team of technologists and insurance enthusiasts, bridging the two worlds together. Check out our About page to learn more. The RoleAbout the RoleAs our GTM Analytics & Strategy hire, you will play a critical role in shaping how Shepherd grows and scales. You’ll work across datasets and systems spanning GTM, underwriting, product, and operations to surface insights that inform strategy, execution, and resource allocation.This is a high-impact, high-visibility role with direct exposure to company leadership. You’ll partner closely with teams across Shepherd to evaluate key business questions, identify growth and efficiency levers, and translate data into clear, actionable recommendations.We value working together in person and are looking for candidates who can be onsite at our San Francisco HQ.ResponsibilitiesDevelop a deep understanding of Shepherd’s business model, GTM motion, and operating cadence to support data-driven decision-makingLead analytical deep dives on core GTM and business questions, identifying patterns, risks, and opportunities across pipeline, conversion, and performanceIdentify, develop, and maintain key performance indicators to measure GTM health, efficiency, and revenue growthCreate and own dashboards and reports using SQL and BI tools to support leadership and functional teamsSupport internal and external reporting requirements, including executive, board, and partner-facing analysesUnderstand and meet key stakeholders’ ongoing analytics needs and deliver actionable, data-driven recommendationsDesign and analyze experiments to test hypotheses and identify scalable growth levers (e.g., activities, segmentation, capacity allocation, GTM prioritization)Maintain, optimize, and establish best practices for BI and GTM toolingEnsure data quality and integrity through robust validation and QA processesYou would be our dream candidate if…5+ years of experience in analytics, business intelligence, data science, management consulting, or a related fieldBonus: experience with revenue, sales, or GTM analytics in a high-growth environmentStrong proficiency in SQL (required); experience with Python is a plusAdvanced Excel skills and experience with modern BI and data visualization toolsExperience analyzing and synthesizing data across Salesforce (CRM) and GTM tooling (e.g., Outreach) to inform pipeline strategy and executionExperience supporting GTM performance management, including quota setting and sales performance trackingExcellent communication skills, with the ability to clearly articulate insights and business implications to technical and non-technical audiencesA high bar for accuracy, rigor, and polish in analytical workStrong business acumen and comfort operating in ambiguityProven ability to prioritize effectively and manage multiple workstreams in a fast-paced environmentA collaborative, low-ego mindset ... (truncated, view full listing at source)