Rollstack
Automate data-driven slide decks and documents with AI
AI Software Engineer (Typescript & LLM)
About the role
The Company
At Rollstack, we are revolutionizing the way businesses share and communicate data and insights. Organizations worldwide rely on slide decks and documents to make informed decisions, whether for leadership, clients, or partners. Yet, preparing these materials often consumes countless hours. Rollstack fully automates that.
We help some of the world's leading organizations, from mid-sized to public companies like SoFi, Zillow and Whirlpool, in automating their slide decks and documents. Headquartered in New York, we offer a remote-friendly workplace and are backed by Insight Partners and Y Combinator, the most successful startup incubator in the world that produced the likes of Airbnb, Twitch, Instacart, Dropbox, Reddit, Doordash, Stripe, Coinbase, etc.
Our team operates with speed and focus to deliver outsized impacts for our customers. We approach every challenge with first principles, never assuming things have to be done a certain way. We are a diverse team that believes intelligence and kindness go hand in hand, welcoming individuals from all backgrounds. Our persistence and rapid execution define us as a category leader and a future generational company.
About the Role
As an AI Software Engineer at Rollstack, you’ll design and ship AI-driven features that transform how teams generate and present data. You’ll work across the stack on LLM-powered workflows, data insights, and automation. This role is perfect for engineers who blend strong fundamentals with creativity to turn AI into real, impactful user experiences.
As an AI Software Engineer, you will
- Design and build user-facing AI features that change how teams generate, analyze, and present data.
- Develop and optimize full-stack workflows that blend responsive React UIs, reliable Node services, and Python-powered AI pipelines.
- Create production-ready LLM solutions for data analysis and content generation using Retrieval-Augmented Generation (RAG) patterns and robust prompt/embedding techniques.
- Integrate with leading BI and content tools, including Tableau, Looker, Metabase, Google Slides, PowerPoint, and Notion.
- Prototype and ship innovations such as generative chart creation, automated report writing, and intelligent data summaries.
- Establish best practices for combining AI with modern web technologies across the stack.
Tech
- TypeScript + React frontend with Tailwind CSS and Shadcn/UI, using modern hooks for composable UI and fast iteration.
- Node.js backend with a sync engine using Prisma ORM and Temporal workflows, powering internal services.
- K8s platform on AWS, deployed with Argo CD for zero‑downtime releases and easy rollbacks.
- Logs in SigNoz, application tracing in Sentry, and product analytics in PostHog.
- Generative‑AI layer powered by OpenAI API, Gemini, LangChain, and Langfuse to deliver automated insights.
- Issue tracking with Linear.
Who We Are Looking For
- 3–8 years of professional software engineering experience.
- Deep expertise in TypeScript, React, and Node.js (3+ years in production).
- Hands-on experience shipping LLM-powered features, ideally with RAG or similar approaches.
- Solid CS fundamentals in algorithms, data structures, and system design.
- Proven collaborator who turns complex ideas into delightful, user-focused products.
Why Join Us
- Join a Y Combinator-backed company that’s redefining how individuals and teams, across industries and around the world, work smarter and faster.
- Work alongside an exceptional team of builders and operators, including alumni from Amazon, Meta, Pinterest, Tesla, and AiFi.
- Be part of a fully remote, globally diverse workplace that values autonomy, impact, and collaboration.
- Contribute to a product that users love and that truly sells itself, built by a world-class product and engineering team.
- Look forward to bi-annual team off-sites in destinations that belong on your travel bucket list.
- Earn competitive compensation and meaningful equity in a fast-moving, high-leverage startup where your work directly shapes the company’s trajectory.
About the interview
At Rollstack, we’re looking for engineers who enjoy iterating, shipping quickly, and solving customers' problems. We want individuals exhibiting a strong sense of ownership and have a get-things-done mentality. Our engineering team defines and drives its technical agenda to continuously iterate on the product and solve our customers' most important problems.
Our interview process is designed to find these kinds of engineers:
- Two technical interviews, one with our CTO and one with one of our engineers. The format is some technical questions and some live coding exercises. We also try to ask questions relevant to the type of product we build. Use the language of your choice during these interviews.
- Two fit interviews with the other cofounders. These are not technical.
About Rollstack
Rollstack is solving the last mile problem in the modern data stack and creating a new category: Reports Automation. We connect BI tools to slide decks and documents, automating their generation and updates.
We help some of the world's leading organizations—from mid-sized to public companies like SoFi, Zillow and Whirlpool—in automating their slide decks and documents. Headquartered in New York, we offer a remote-friendly workplace and are backed by Insight Partners and Y Combinator, the most successful startup incubator in the world that produced the likes of Airbnb, Twitch, Instacart, Dropbox, Reddit, Doordash, Stripe, Coinbase, etc.
Our team operates with speed and focus to deliver outsized impacts for our customers. We approach every challenge with first principles, never assuming things have to be done a certain way. We are a diverse team that believes intelligence and kindness go hand in hand, welcoming individuals from all backgrounds. Our persistence and rapid execution define us as a category leader and a future generational company.
