What We Do

Yesterday's insurance wasn't built for today's risk. We see it in the data and we feel it in the field. Emerging technology can reinvent how risk is priced and managed, faster and smarter, anchored in proven expertise. First-movers will define the next era of commercial risk management, and Shepherd is building it.

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

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, led our Series B round

• Costanoa Ventures, led our Series A round

• Spark Capital, led our Seed round

• Susa Ventures, lead our Pre-Seed round

• Y Combinator

• 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.

About You

As our first Revenue Operations hire, you will play a critical role in shaping how Shepherd grows and scales. You’ll work across datasets and systems spanning GTM, underwriting, marketing, 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 GTM questions, identify growth and efficiency levers, and translate data into clear, actionable recommendations.

About the Role

Shepherd is looking for our first Revenue Operations hire to be the operational backbone of our GTM team. This role sits at the intersection of strategy and execution — you'll partner closely with GTM leadership to improve how our team operates, identify what's working and what isn't, and build the systems and processes that help us scale. You're someone who understands the mechanics of GTM motions deeply and technical enough to independently navigate our internal tooling and data.

We value working together in person and are looking for candidates who can be onsite at our San Francisco HQ.

Responsibilities

GTM Operating Cadence

• Serve as a strategic business partner to GTM leadership — supporting pipeline reviews, forecast calls, and QBRs with rigorous, well-structured analysis

• Own the operating rhythm of the GTM team: weekly reporting, pipeline hygiene standards, and performance tracking against targets

• Identify bottlenecks and inefficiencies in the GTM process and lead initiatives to address them

• Translate GTM strategy into operational plans, ensuring alignment between leadership priorities and day-to-day execution

Planning & Strategy

• Manage territory planning and segmentation, ensuring coverage is optimized as the team grows

• Own quota setting and sales compensation design in partnership with Finance and GTM leadership — modeling scenarios, stress-testing assumptions, and managing the annual and mid-year cycle

• Support headcount planning and capacity modeling to inform hiring decisions and revenue targets

• Design and analyze experiments to test GTM hypotheses — segmentation changes, coverage models, prioritization frameworks

Systems, Data & Tooling

• Comfortable managing and improving Shepherd's sales tech stack, including Salesforce and Outreach — maintaining data integrity, managing configurations, and evaluating new tools as needs evolve

• Build and maintain dashboards and reports that give leadership real-time visibility into pipeline, conversion, and performance

• Ensure CRM hygiene and data quality through clear standards, enforcement mechanisms, and regular audits

• Partner with Analytics and Business Operations to surface insights from GTM data, translate them into actionable recommendations, and execute against them

What We're Looking For

• 6+ years of experience in Sales Operations, Revenue Operations, or a closely related role at a high-growth company

• Deep familiarity with sales motions and GTM mechanics — you understand how pipelines work, how B2B sales teams operate, and how to diagnose performance gaps

• Strong Salesforce skills; experience with Outreach or similar sales engagement tooling a plus

• Proficiency in SQL and Excel/Sheets for data analysis and modeling; experience with BI tools (e.g., Metabase, Looker, Hex, Sigma, etc.)

• Experience owning quota and comp planning processes, including cross-functional coordination with Finance

• Highly organized with strong process instincts — you create structure where there isn't any and maintain it under pressure

• Clear communicator who can present data and recommendations to leadership

• Collaborative, low-ego, and comfortable working across functions in a fast-paced environment

How we work

Shepherd runs on four values. Here's what each one means in this seat.

• Think big, build big. We exist to protect progress and the industries that rely on it. The work here is aimed at a system that runs on its own, and the roadmap gets sequenced backward from that rather than forward from what's easy.

• Win together. We rise as one. We support each other, raise the bar, and celebrate collective success. As the first PM you set a standard the rest of the team inherits, and the milestones belong to the team rather than to product.

• Cross the aisle. Collaboration wins. We listen deeply, work across boundaries, and prioritize shared success over individual lanes. The best product calls here come from engineers who've sat with underwriters and underwriters who understand where the model breaks, and much of this job is listening closely enough on both sides to make that happen.

• Go get it. We act with urgency, move with confidence, take smart risks, and push forward with intention. Nobody hands you the roadmap, the data, or the meeting invite. You pull the failing runs, book the time with the underwriters, and decide what matters.

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