Founding Engineer for AI-native Investment Bank

What we're looking forRowan is hiring a Founding Engineer: the person who takes our platform from local to production and runs the engineering team that keeps it shipping.You've done this before. Either you've founded a company and built the product yourself, or you led engineering at a startup from pre-seed or seed through a Series A or B. You know what it takes to go from a few engineers and a working prototype to a reliable product that real customers depend on every day.You'll partner directly with our CEO and Co-Founder. They set what we build and why. You own how and when it gets built, and you make sure it ships.No M&A or investment banking experience is needed. You do need some comfort with finance and accounting, because you'll work every day alongside our FDDs, controllers, investment bankers and transaction advisors.Who we areRowan is a seed stage venture backed startup, AI-native investment bank that helps founder-led industrial businesses in the lower middle market ($10-100M enterprise value) sell to strategic, family offices, and private equity buyers. Our platform takes in a company's messy financial and operational data, cleans and organizes it into a structured database, and powers the analysis our bankers use to run a deal. The goal is simple: increase the value of the businesses we represent, and sell them faster.We're a small team of engineers, bankers, controllers and diligence specialists. Our CEO previously built and sold Machinio, the largest online machinery marketplace.

Location: Chicago, IL (River North), in personCompensation: $150,000 to $200,000 base, plus equityWhat you'll ownProduction.

Take our platform from local development to a production system bankers and clients rely on. Own deployment, CI/CD, monitoring, uptime and security.Delivery. Run project management for engineering: sprint planning, a weekly release rhythm, clear priorities and honest timelines.The team. Lead and mentor our engineers today, then hire and build the team as we grow.Architecture. Make the calls on how we structure our data pipelines, AI systems and core platform so they hold up as deal volume grows.Product partnership. Work with the CEO and our bankers to turn what they need into a roadmap engineering can ship. Push back when something won't work, and propose what will.Hands on keyboard. This is a builder's role. Expect to write code and review it, especially in your first six months.Who you areMust haveOne of these two backgrounds:You founded a company and built its product, whatever the outcome, orYou led engineering at a startup from pre-seed or seed through Series AYou've taken a product from prototype to a production system with real users and real uptime expectationsYou've managed engineers and run a delivery process, not just written codeYou still like to build, and you're comfortable shipping between meetingsYou make product calls based on what users actually need, and you can explain themYou're comfortable with ambiguity and a lot of autonomyNice to haveExperience in fintech, accounting, or other data-heavy B2B softwareProduction experience with LLMs, RAG or agent systemsExperience building ETL or data pipelines at scaleExperience hiring an engineering team from the first few engineers onwardOur tech stackThis is what we build with today. You'll help decide where it goes next, and direct experience with every tool isn't required.Frontends: React in TypeScript; Postgres-backed authenticationBackends: FastAPI in Python; Express in TypeScriptData and infrastructure: Postgres and S3; Redis instances and workersGenerative AI: LLMs, RAG, agentic memory and code-execution harnessesDevelopment: GitHub, Prisma ORM, AI coding agents, AI code reviewVisibility: Sentry for observability, PostHog for product analyticsOur interview processIntro call (30 min): with our CEO, about your background and what you're looking forExperience deep dive (60 min): walk us through a product you took from early stage to production, the team you built and the calls you'd make differentlyCase study (take-home, about 2 hours): an open-ended build in our case study repo. We're testing product sense: what you chose to build, and why. AI assistance is welcome.Onsite (half day, Chicago):Walk through your case studyLive system design: a production AI system that processes an adjusted trial balancePlanning session: build a 30-day plan for our engineering team from our real backlogMeet our bankers, FDDs and controllersReferences: including at least one person you managed and one founder or exec you worked for