AI Software Engineer

AI Software Engineer – Automotive Deal Sourcing & Marketplace Automation Location: Chicago, IL / Remote Employment Type: Full-Time, Part-Time, or Contract We are a Chicago-based automotive business looking for an experienced Software Engineer with AI, automation, and data-analysis skills to help us build a system that identifies profitable used-car purchasing opportunities. Our goal is to find good vehicles at the right price from sources such as: Facebook MarketplaceCraigslistOfferUpPublic/private sellersDealer listingsAutomotive auctionsWholesale marketplacesOther online vehicle sourcesWhat We Want to BuildWe want an AI-powered vehicle acquisition platform that helps answer: “Which cars should we buy today, and what is the maximum price we should pay?” The system should be able to: Collect and organize vehicle listings from multiple permitted sources.Identify newly posted and potentially underpriced vehicles.Extract year, make, model, trim, mileage, VIN, price, location, description, and other available information.Compare asking price with wholesale and estimated retail value.Estimate repair/reconditioning costs.Calculate potential gross profit and ROI.Recommend a target purchase price and maximum bid.Generate a Deal Score / Buy Score.Alert buyers when strong opportunities are identified.Analyze seller descriptions using AI.Use image analysis to help identify visible vehicle damage or condition issues.Identify potentially high-risk vehicles.Analyze auction listings and condition reports.Track vehicles, negotiations, acquisition decisions, repairs, and final sales.Learn from historical purchases and sales to improve future buying recommendations.Build dashboards showing the best current acquisition opportunities.Example Output2015 Toyota Camry Mileage: 118,000 Seller Asking: $6,000 Estimated Wholesale Value: $6,800 Estimated Retail Value: $9,000 Estimated Repairs: $600 Target Purchase Price: $5,200 Maximum Buy Price: $5,600 Estimated Gross Profit: $2,800 Deal Score: 91/100 — Strong Buy Preferred Technical SkillsWe are interested in candidates experienced with: PythonJavaScript / TypeScriptAI / Machine LearningOpenAI API or other LLM platformsAPIs and third-party integrationsSQL / PostgreSQLData pipelinesBrowser automationWeb applicationsData extractionComputer vision / image analysisCloud deploymentGit / GitHubDashboard developmentExperience with any of the following is highly desirable: Automotive industryUsed-car dealershipsVehicle auctionsVIN decodingVehicle pricing modelsAutomotive data providersMarketplace applicationsRecommendation enginesPredictive analyticsMarketplace integrations must be designed using authorized APIs, compliant data-access methods, or human-in-the-loop workflows where required by platform rules. Who We Are Looking ForWe do not want someone who simply waits for programming instructions. We want an engineer who can understand the business objective and help design the solution. The key question is: How can technology help us find undervalued vehicles before other buyers find them? You should be entrepreneurial, analytical, creative, and interested in building a real-world AI product that directly affects purchasing and profitability. To ApplyPlease send: Resume or LinkedIn profileGitHub or portfolioExamples of AI/automation projectsExperience working with APIs or large datasetsAny automotive experienceCompensation expectationsPlease also answer: If Facebook Marketplace, Craigslist, OfferUp, auctions, dealers, and other sources collectively contained 50,000 vehicles today, how would you design a system to identify the best 20 vehicles for us to purchase?