Founding AI Engineer

Chief AI is building the intelligence platform to power the world's leaders. The relationships, data, and institutional knowledge that drive consequential decisions today live across inboxes, calendars, documents, and memory. We are building the system that turns that fragmented information into a structured context and intelligence layer for leaders and their teams, from Mayors to Congressmen to CEOs. We are VC-backed, a Stanford StartX company, and actively deployed with customers in government and enterprise. We won 1st place at the US Conference of Mayors and "Most Innovative Startup" at State of GovTech. Our founder previously worked for leaders in the White House, Congress, and tech c-suites and is building the solution her teams always needed. See more from our launch at SXSW and Axios. About The Role We are hiring a Founding AI Engineer to build the systems that define a new category of intelligence for executive teams. You will work on everything – backend, frontend, AI, infrastructure, and security – shaping product direction and engineering culture from day one. This is a genuinely hard technical problem. We are building a context graph that connects people, organizations, events, communications, and institutional knowledge into a system that AI can reason over accurately, securely, and reliably. The product sits at the intersection of AI-powered intelligence, data infrastructure, and agentic workflows. If you thrive in ambiguity and love shipping fast, this role is for you. What You'll Do Within weeks Ship core agent features and evals that executive teams rely on day-to-day Build ingestion pipelines and structure data to create actionable context Work directly with customers to understand how their offices operate and where Chief AI can embed in their daily workflows Within months Help shape Chief AI's core architecture and AI workflows for executive reasoning and decision-making Build upon personalization and intelligence used across briefings, tasks, and relationships Prototype and iterate with voice-to-text, surfacing recommendations, and more Help set the engineering hiring bar and culture as founding engineer, including scouting and hiring as the team scales What We're Looking For 4+ years of experience shipping full-stack, production-grade products Early-stage startup experience building 0 to 1; founding or early ( Strong engineering fundamentals across scalable backend systems, infrastructure, and production software; fluency with AWS, Python, and React Experience shipping AI-native products, including work with agents, LLMs, context graphs, retrieval systems, evals/observability, and other modern AI tooling Fluent using AI across product development: prototyping, coding, testing, and going from idea to production in hours Strong product instincts; a high bar for quality, craft, and design Customer obsessed; ability to meet with customers, find pain points, and translate them into technical solutions High-agency; moves quickly, makes decisions with incomplete information, and takes ownership of outcomes Bonus: experience building secure, reliable systems in a regulated environment (AWS GovCloud, FedRAMP, SOC2, or similar) Bonus: experience working with government and/or regulated industries U.S. citizen (required for security clearance as needed) Why Join Chief AI? Build AI for decision-makers: you'll be able to point to real leaders – mayors, congressmen, CEOs – and know your work helped power offices that impact millions Own the intelligence layer from day one: a truly hard technical challenge to turn messy executive context into briefings, strategy, and decisions Founding ownership: ship end-to-end, work directly with customers, and help define the technical DNA of the company Work directly with the CEO and founding team building a category-defining product at the intersection of AI, relationships, and decision-making Meaningful equity with competitive salary, benefits, and significant long-term upside Ready to build the intelligence platform for the world's leaders? #J-18808-Ljbffr Chief Software Inc.