GTM Analytics & Strategy

In March 2026, Shepherd raised a $42M Series B — 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

Spark Capital

Costanoa Ventures

Y Combinator

Susa Ventures

And several others

We're a team of technologists and insurance enthusiasts, bridging the two worlds together. Check out our About page to learn more.

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 .

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

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

📚 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