Revenue Operations Manager in Chicago, Illinois at Letter AI

Revenue Operations ManagerLocation: Chicago, IL (Hybrid, in-office 3 days per week) Team: Go-To-Market Type: Full-time
About Letter AILetter AI is the world's first unified revenue acceleration platform powered natively by generative AI. Our platform empowers sales teams at customers like Lenovo and Redpanda to ramp up faster with AI-powered training and coaching, instantly find and personalize collateral for customers, and engage their buyers with the industry's first AI Sales Room. We recently raised a $40M Series B led by Battery Ventures, with participation from existing investors including Y Combinator, Lightbank, Northwestern Mutual Future Ventures, Stage 2 Capital, and Formus. The round comes just four months after announcing our Series A, indicating a shift we're seeing in real time: revenue teams aren’t asking for more content or tools. They’re asking for better outcomes, and Letter AI is bringing those outcomes to life! We 10Xed our revenue last year and are looking for the best of the best in Chicago to join us on the adventure 📈.
About the RoleWe are hiring a Revenue Operations Manager to help build and scale the operational foundation of our go-to-market organization. This is a high-impact individual contributor role that partners closely with Sales, Marketing, and Customer Success leadership to ensure our systems, data, and operating rhythms support predictable, efficient growth.You will sit at the intersection of data, systems, and execution, owning the processes and insights that drive how revenue teams operate day to day. This role is both strategic and hands-on, ideal for someone who enjoys solving operational problems and building systems that scale alongside a fast-growing company.This role is based in Chicago, with an expectation to work from our office three days per week to enable close collaboration with leadership and cross-functional teams.What You’ll OwnRevenue Operations & GTM Execution

• Own and evolve core RevOps processes, including pipeline management, forecasting, account planning, and deal execution workflows.
• Partner closely with Sales leadership to maintain pipeline quality, improve forecast accuracy, and support consistent operating cadence.
• Identify risks and opportunities across the funnel and proactively recommend operational improvements.
• Support quarterly and annual planning processes, including capacity modeling and performance tracking.
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Data, Systems & Tooling

• Own data accuracy, governance, and hygiene across Salesforce and the broader GTM tech stack.
• Design scalable workflows and automation that reduce manual effort and improve data reliability.
• Manage system integrations and ensure consistent data flow across GTM systems.
• Evaluate and implement AI-enabled tools that improve revenue productivity and operational efficiency.
• Collaborate closely with the Data Analyst to align GTM reporting, maintain consistent metric definitions, and ensure data models support forecasting, pipeline visibility, and executive reporting needs.

Analytics & Insights

• Build and maintain reporting across pipeline, forecasting, conversion, and revenue performance.
• Translate complex data into clear, actionable insights for GTM and executive leadership.
• Establish consistent definitions and reporting standards across teams.
• Support executive and board-level reporting with reliable and scalable analytics.
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Cross-Functional GTM Alignment

• Partner with Sales, Marketing, and Customer Success to ensure alignment across the full revenue lifecycle.
• Support pricing workflows, deal approvals, and operational components of commission processes.
• Lead cross-functional initiatives that require strong coordination and change management.
• Help operationalize new GTM initiatives and processes as the organization grows.
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What We’re Looking For

• 4–7 years of experience in Revenue Operations, Sales Operations, or GTM Operations at a high-growth SaaS company.
• Strong experience with Salesforce and modern GTM tooling ecosystems.
• Experience using automation or AI-enabled tools to improve operational workflows.
• Strong analytical mindset with the ability to translate data into clear business decisions.
• Experience building dashboards and working with core revenue metrics such as pipeline coverage, forecast accuracy, and conversion rates.
• Ability to operate independently in a fast-paced environment with evolving priorities.
• Strong communication skills and ability to work cross-functionally with senior stakeholders.
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Why This Role MattersLetter is scaling quickly, and the systems and processes built now will define how efficiently we grow over the next stage of the company. This role has direct impact on how confidently we forecast, how effectively our teams execute, and how well our GTM organization scales as we continue to expand.This is a role for someone who wants meaningful ownership and the opportunity to grow alongside the company as Revenue Operations continues to evolve.