GTM Analytics & Strategy

WHAT WE DO

Shepherd is an AI-native commercial insurance platform transforming how high-hazard industries get covered. 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.

The infrastructure behind the AI boom — data centers, semiconductor fabs, renewable energy assets — has to be built and insured. But traditional carriers weren't built for this speed:

• Complex commercial construction projects routinely wait weeks for a single quote
• Legacy carriers rely on static applications and disconnected systems
• Brokers chase carriers through calls, emails, and resubmissions

We built Shepherd to solve that. Our AI performs the same underwriting workflows in seconds, and integrates real-time data from construction technology partners — Procore, Autodesk, OpenSpace, DroneDeploy, and others — to see risk as it actually exists, not just as it was reported on a static form.

We're pursuing the most ambitious technical vision in commercial insurance: fully autonomous underwriting. We're closing in on the first fully agentic submission in the industry — email in, price out, no human intervention until the last mile.

With Shepherd, safety, speed, and quality no longer trade off against one another — they compound. We're building:

• Faster decisions
• Smarter, more accurate pricing
• Better risk outcomes for insureds who invest in safer practices

We're not just modernizing insurance products. We're building the risk infrastructure for the next generation of financial services.

OUR INVESTORS

In March 2026, Shepherd raised a $42M Series B https://www.linkedin.com/posts/justindlevine29_today-were-announcing-our-42m-series-b-activity-7442200922291630080-z1gw?rcm=ACoAAAkOMEwBRnAAXmdnQcaOJeioCu6VCqR6Gzc&utm_medium=member_desktop&utm_source=share — 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 https://www.intactfc.com/about-us/intact-ventures
• Spark Capital https://www.sparkcapital.com/
• Costanoa Ventures https://costanoa.vc/
• Y Combinator https://www.ycombinator.com/
• Susa Ventures https://www.susaventures.com/
• And several others

OUR TEAM

We're a team of technologists and insurance enthusiasts, bridging the two worlds together. Check out our About https://www.shepherdinsurance.com/about page to learn more.

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

🥕 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