GTM Analytics & Strategy
What We Do
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
To date, Shepherd has raised over $20M from leading investors, including:
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.
The Role
About the Role
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.
Responsibilities
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
You would be our dream candidate if…
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
Interview Process
Recruiter Screen
Hiring Manager Interview
Take-Home Assessment
Team Member Interview
Final Onsite Interviews at our SF HQ
#LI-Onsite
Benefits
🏥 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