Principal Software Engineer, Applied AI

About Highspot Highspot is pioneering the category that is fundamentally changing the way companies increase sales productivity. On a mission to transform the way millions of people work with sales enablement, Highspot is committed to building breakthrough software with a spark of magic. We believe a great place to work is about more than the work – it’s about what the company stands for, and how it authentically represents its values in the real world. To this end, we have put intentional focus on creating equitable workspaces for each of our employees. Our goal is to create a culture where everyone feels a deep sense of belonging and is empowered to be an agent of change, with the ability to transform themselves, their workplace, and their world. About the Role We are looking for a Principal Software Engineer to join our Applied AI team. This is a rare opportunity to work at the cutting edge of Generative AI and Agentic systems – applied directly to high-impact business problems at enterprise scale. Highspot's AI challenges are uniquely interesting: our platform ingests millions of heterogeneous enterprise documents (slides, PDFs, spreadsheets, CRM records, analytics data), and our AI agents must reason across all of it to surface actionable insights for sales teams. You'll tackle problems spanning context engineering, multi-step agentic orchestration, retrieval and ranking over diverse content types, and evaluation of non-deterministic systems – all within the constraints of enterprise-grade reliability, multi-tenant security, and cost efficiency. As the Principal Engineer on the Applied AI team, you will own the technical direction for Generative AI and Agentic solutions across Highspot. You'll set the architecture, ship production systems, and raise the AI engineering capability of the broader organization. You will work closely with machine learning experts, data scientists, product managers, and engineering leadership to drive high-impact business outcomes.