Letter AI

Own the entire data lifecycle including real-time ingestion pipelines, data transformation, and building executive dashboards. | Strong software engineering, proficiency with cloud data platforms, expert SQL, and advanced dashboard building skills are required. | Data Engineer Chicago Go-To-Market Chicago or San Francisco, Hybrid (3 Days In-Office) Full-time About Letter AI Letter AI [https://www.letter.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. The Role We are looking for a highly technical Data Engineer who possesses the analytical mindset of a Data Analyst. You must be as comfortable architecting real-time ingestion pipelines as you are building executive-facing dashboards. We need a hands-on builder who understands software engineering and can operate independently without heavy engineering support. The ideal candidate is someone who doesn't just "move" data, but understands the "why" behind it. You will own the entire lifecycle of data at Letter AI—from raw ingestion out of S3 and other sources, to the complex cleanup and transformation within your data platform (Databricks/Snowflake), to the final visualization that drives business decisions. We need a technical powerhouse who ensures data is never a bottleneck. Your key responsibilities will include: * Full-Lifecycle Data Ingestion: Architect and manage robust pipelines to ingest data from diverse sources (S3, Salesforce, internal APIs) into a centralized platform like Databricks or Snowflake, ensuring all data is kept up to date in real-time. * Data Engineering & Cleanup: Once data is ingested, you will be responsible for the heavy lifting of cleaning, normalizing, and structuring messy datasets within Databricks to ensure high data integrity and performance. * End-to-End Analytics: Act as the primary Data Analyst for the GTM and Product teams. You will translate raw data into meaningful insights by building and maintaining sophisticated visualizations in Tableau or Power BI. * Independent Infrastructure: Set up and manage the data environment (Databricks, Integrations, etc.) from the ground up without needing constant support from the core software engineering team. * Transformation Layer: Use dbt and SQL to build a scalable transformation layer that serves as the "single source of truth" for the entire company. * Partnership: Work closely with leadership to define KPIs and then build the automated tracking systems to monitor them. Qualifications for the role include: * The Ideal Skillset: You are both a Data Engineer and an Analyst. You can write the Python code to scale an ingestion engine and the SQL to build a complex cohort analysis. * Strong understanding of software engineering principles; you should be comfortable working in a technical environment and solving "bottleneck" issues independently. * Experience setting up and managing modern cloud data platforms (Databricks, Snowflake, etc.) and ingesting data from cloud storage (S3). * Advanced proficiency in building automated, high-impact dashboards in Tableau or Power BI. * Expert-level SQL skills for data cleaning, transformation, and modeling (experience with dbt is a major plus). * Familiarity with Salesforce (SFDC) and GTM data structures. * Expertise in using AI tools (e.g., GitHub Copilot, Claude, ChatGPT) to accelerate coding, debugging, and analysis. * 2-5 years of hands-on experience in a technical data role, preferably in a fast-paced startup environment. As a part of the team at this early stage, you will not only receive a competitive salary and benefits, but also an equity stake in the company. How We Operate At Letter AI, we want you to be unapologetically you while operating with our core principles in mind: * Customer-obsessed: Make your customers unreasonably happy and everything else will fall into place. * Ambitious yet practical: Set big goals, but stay grounded with disciplined execution and ruthless prioritization. * Direct yet kind: Never hold back from speaking your mind, but do so in a way that is kind to your colleagues. * Driven yet humble: Push for excellence and deliver fast, but keep your humility.  Join us on this exciting journey to build the world's next generational sales tech company. We look forward to hearing from you!

Providing executive and administrative support to senior leadership and managing operational processes. | Experience supporting C-level executives and managing operational and administrative functions in dynamic environments. | Revenue Operations Manager Location: Chicago, IL (Hybrid, in-office 3 days per week) Team: Go-To-Market Type: Full-time About Letter AI Letter AI is building the world’s first AI-native unified revenue enablement platform. We help global revenue teams operate faster and more effectively by bringing learning, content, coaching, and deal execution into a single system powered by AI. Our customers include some of the most forward-thinking GTM organizations in the world, and we are scaling quickly as enterprise teams move away from fragmented tooling toward unified, AI-driven workflows. As we grow, operational execution becomes increasingly important, and Revenue Operations plays a central role in how we scale. About the Role We 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 Own Revenue 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. 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. 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. 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. Why This Role Matters Letter 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.