Revenue Operations

About the role

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.

Responsibilities

• 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
• 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
• 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

Qualifications

• 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