Contextual AI

Job Overview Contextual AI is building out its founding GTM team and is seeking an experienced Revenue Operations Analyst to catalyze new business acquisition, growth, and scale. This role ensures the revenue team has the supporting systems, processes, and insights required to win. Reporting directly to the Head of Revenue Operations, you'll own day-to-day GTM systems and reporting while also recommending improvements to optimize the revenue operating model. This is a high-impact role with exposure to senior leadership, and the opportunity to help shape how Contextual AI scales its GTM engine in a rapidly growing AI market. What You'll Do Own the GTM systems stack — optimize how tools are used and integrated to support Contextual AI's goals. Partner across Sales, Marketing, and Customer Success to support daily operational needs and ensure smooth revenue workflows. Analyze sales data and generate actionable insights through reports and dashboards covering pipeline coverage, deal progression, forecast accuracy, and renewals. Identify and drive process improvements to streamline/automate sales workflows and enhance CRM data hygiene. Enable a high-velocity outbound sales motion by leveraging enrichment tools and processes to seed campaigns with best-fit accounts and contacts. Support revenue planning activities such as quarterly business reviews (QBRs), territory design, and compensation modeling with accurate, timely data. What We're Seeking 3–4+ years of experience in Sales Operations, Revenue Operations, or Sales Analytics. Demonstrated experience partnering with U.S.-based sales and operations teams, with the ability to work ET/PT hours. Proficiency in Salesforce CRM, including Salesforce Flows and managing integrations to other revenue tools. Salesforce certifications are a plus, but not required. Experience with Clay or comparable enrichment/engagement platforms. Familiarity with other revenue tools such as LeanData, Gong, and Outreach. Proven ability to analyze large datasets and distill insights into clear, actionable recommendations. Solid understanding of GTM motions including pipeline management, opportunity lifecycle, renewals, and account planning. Strong communication and collaboration skills with the ability to influence cross-functional stakeholders. Highly organized and able to manage multiple priorities in a fast-paced environment.