GTM Analytics & Strategy

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.

To date, Shepherd has raised over $20M from leading investors, including:

• Spark Capital

• Costanoa Ventures

• Y Combinator

• Susa Ventures

• Intact Ventures

• And several others

We're a team of technologists and insurance enthusiasts, bridging the two worlds together. Check out our team page to meet some of us!

As 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.

• Develop a deep understanding of Shepherd’s business model, GTM motion, and operating cadence to support data-driven decision-making

• Lead analytical deep dives on core GTM and business questions, identifying patterns, risks, and opportunities across pipeline, conversion, and performance

• Identify, develop, and maintain key performance indicators to measure GTM health, efficiency, and revenue growth

• Create and own dashboards and reports using SQL and BI tools to support leadership and functional teams

• Support internal and external reporting requirements, including executive, board, and partner-facing analyses

• Understand and meet key stakeholders’ ongoing analytics needs and deliver actionable, data-driven recommendations

• Design 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 tooling

• Ensure data quality and integrity through robust validation and QA processes

• 5+ years of experience in analytics, business intelligence, data science, management consulting, or a related field

  • Bonus: experience with revenue, sales, or GTM analytics in a high-growth environment

• Strong proficiency in SQL (required); experience with Python is a plus

• Advanced Excel skills and experience with modern BI and data visualization tools

• Experience analyzing and synthesizing data across Salesforce (CRM) and GTM tooling (e.g., Outreach) to inform pipeline strategy and execution

• Experience supporting GTM performance management, including quota setting and sales performance tracking

• Excellent communication skills, with the ability to clearly articulate insights and business implications to technical and non-technical audiences

• A high bar for accuracy, rigor, and polish in analytical work

• Strong business acumen and comfort operating in ambiguity

• Proven ability to prioritize effectively and manage multiple workstreams in a fast-paced environment

• A collaborative, low-ego mindset and experience working cross-functionally

• Recruiter Screen

• Hiring Manager Interview

• Take-Home Assessment

• Team Member Interview

• Final Onsite Interviews at our SF HQ

#LI-Onsite

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

🏖️ 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, or Dallas-Fort Worth Offices
Premium office spaces on both coasts with daily lunches provided

📚 Professional Development
Access to premium coaching, including leadership development

🏦 401(k) Plan
Competitive 401(k) plan offered

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