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Job Title


Founding AI Product Engineer


Company : Olivia


Location : winnipeg, Manitoba


Created : 2026-05-08


Job Type : Full Time


Job Description

IMPORTANT: TO APPLY, PLEASE COMPLETE THE TEST AT THE FOLLOWING LINK:https://tally.so/r/3l2WzVWe review every applicant who completes the test. The posting closes in approximately 4 days.About Olivia AIOlivia is the AI brand designer for e-commerce. Brands use Olivia to generate professional product photography, ad creatives, and marketing assets through natural conversationin minutes, not months.Were replacing the fragmented, expensive workflow of agencies, freelancers, and manual design tools with a single AI-native platform that handles everything from product shot generation to campaign-ready ads. Our customers range from scaling DTC brands to enterprise retailers.Join us as we build the operating system for visual commercea $178.8B market thats being completely reshaped by AI.The Opportunity: Applied Agentic DeveloperWere hiring our first engineer. This is a founding rolenot a ticket-taker position.An Applied Agentic Developer at Olivia is a builder who ships end-to-end: youll own features from concept through production, make product decisions, and push code daily. You think like a founder, design with user empathy, and write code that works at scale.Youll be working directly with our CTO on the hardest problems in AI-powered creative tooling: real-time image generation pipelines, canvas-based editing systems, multi-model orchestration, and conversational UX that actually feels intelligent.This role requires creativity, speed, and comfort with ambiguity. If you need a detailed spec before you start building, this isnt the right fit. If you get excited about shipping something rough, getting user feedback by end of day, and iterating fastkeep reading.Why Join OliviaFirst Engineering Hire: Shape the technical foundation and culture from day one. This is the ground floor.Founder-Level Impact: Work directly with the co-founders. Your ideas will ship, not sit in a backlog.Real Product, Real Users: Olivia is live with paying e-commerce brands. Youll see the impact of your work immediately.Equity Path: Potential equity options at specific tenure and milestone achievements.Remote-First, High-Agency: No performative meetings. We care about output, not hours logged.A Day in the LifeWe want to be transparent about how we work. Heres what a typical day looks like:Start with a quick, high-context standup to align on priorities.Dive into building with AI-native tools like Cursor and Augmentrapidly implementing and iterating on generative, agentic, and conversational features.Collaborate with the founding team via Slack and Loomsharing progress, demoing builds, and brainstorming solutions async.Push code daily. We believe in accountability and tangible progress.Spend time not just coding, but thinkingcreating mockups, questioning assumptions, and proactively suggesting improvements.Work across the three AI pillars that define Olivia: Generative (image/asset creation), Agentic (autonomous design decisions), and Conversational (natural language control).Who You AreThe short version:01 Builder Ex-founder or founding engineer whos shipped product from scratch.Relentless Fixer Turns blockers into shipped features. Doesnt wait for permission.Autonomous Operator Thrives in ambiguity. Creates structure, doesnt need hand-holding.AI-Native Already building with agents, model APIs, and tools like Codex. Understands when to leverage AI and when to apply human judgment.Design Instinct You dont build ugly things. Even without formal design training, your UX sense is strong.Startup DNA Loves small teams, big impact, full ownership. Brings energy, not ego.Your Approach & MindsetProactive, Not ReactiveYou dont wait for detailed specs. You anticipate needs, experiment with solutions, and bring concrete ideas to the table. When asked to build a button, you come back with three interface concepts and explain the UX implications of each.AI-Accelerated DevelopmentYou have real, hands-on experience using tools like Cursor and Augment to dramatically accelerate your workflow. You know how to effectively partner with AI to build complex applicationsand you know when to override it.Rapid LearnerWhether self-taught or formally trained, you absorb new concepts fast. Youre equally comfortable diving into diffusion model architectures as you are mastering a new frontend framework. Unfamiliar territory is an invitation, not a barrier.Clear CommunicatorYou articulate technical concepts and creative ideas to diverse audiencesengineers, designers, non-technical stakeholders. In a fast-moving startup, your communication prevents costly misunderstandings and keeps everyone aligned.Ownership MentalityYou take pride in your work. You understand that building something meaningful from zero requires both technical excellence and cultural contribution. Youre not just writing codeyoure building a company.Proven Track RecordYou have concrete evidence of shipping products real users depend onwhether from professional experience, personal projects, or open-source contributions. You write clean, maintainable code and understand the full product lifecycle.Core ResponsibilitiesEnd-to-End Product DevelopmentArchitect, build, and launch features from concept to production. Own technical design, deployment, and post-launch iteration. Youre the driving force behind features that directly shape user workflows.AI Pipeline DevelopmentBuild and optimize Olivias generative image pipelinesincluding model orchestration, image segmentation, inpainting, and prompt engineering. Work with APIs from OpenAI, Anthropic, Bedrock, and Google AI to create intelligent, multi-model workflows.Canvas & Editor ArchitectureDevelop and iterate on Olivias real-time canvas editing experiencehandling asset manipulation, layer compositing, resize logic, and interactive design tools that feel intuitive and responsive.Conversational UXBuild the conversational layer that lets users control Olivia through natural languagetranslating brand context, creative intent, and design preferences into generated outputs that feel on-brand.User-Obsessed DevelopmentWrite code with deep user empathy. Think constantly about e-commerce brand workflows, pain points, and moments of delight. User experience is your North Star.Scalable InfrastructureDesign cloud-native systems using Cloudflare Workers, R2, Postgres, and modern infra tooling. Build for everything from single user requests to enterprise-scale batch operations.Product Vision & RoadmapProactively shape Olivias futureidentifying opportunities across product photography, ad generation, email creative, and video. Push the boundaries of what AI-powered creative tools can do.Tech Stack & ToolsWe dont expect you to know everything, but strong experience with our core stack is essential.Core: TypeScript/JavaScript (Node.js, React). Youll pick up Wasp quicklyits built on Node/React. Python experience is a plus.AI/ML: Experience working with generative image models, LLM APIs, prompt engineering, and model orchestration. Familiarity with image segmentation (SAM), diffusion models, or LoRA fine-tuning is a strong bonus.AI Dev Tools: Augment (our primary tool), Cursor.Platforms & APIs: Cloudflare (R2, Workers), AWS/GCP, Amazon Bedrock, Google AI, OpenAI, Anthropic.Infrastructure: PostgreSQL, Docker, Git, Linear.Hiring ProcessWe want to find the right long-term partner, so our process is designed for great mutual fit.Application: Submit your application and show us what youve built.Technical & Culture Interview: A conversation with our CTO to get to know each other, discuss your experience, and align on the future of AI-powered creative tools.Paid Demo Project (12 Weeks): Top candidates work on a paid, real-world project. Youll see how we work, and well see you in action.Offer: If its a great fit for both sides, well make a full-time offer with potential equity options at specific tenure and milestone achievements.Ready to Build the Future of AI-Powered Creative?If youre excited about pushing the boundaries of what AI can do for visual commerceand you want to be the first engineer at a company thats reimagining how brands createwe want to hear from you.Apply now: https://tally.so/r/3l2WzV