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 Marketplace
- Craigslist
- OfferUp
- Public/private sellers
- Dealer listings
- Automotive auctions
- Wholesale marketplaces
- Other online vehicle sources
What We Want to Build
We 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 Output
2015 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 Skills
We are interested in candidates experienced with:
- Python
- JavaScript / TypeScript
- AI / Machine Learning
- OpenAI API or other LLM platforms
- APIs and third-party integrations
- SQL / PostgreSQL
- Data pipelines
- Browser automation
- Web applications
- Data extraction
- Computer vision / image analysis
- Cloud deployment
- Git / GitHub
- Dashboard development
Experience with any of the following is highly desirable:
- Automotive industry
- Used-car dealerships
- Vehicle auctions
- VIN decoding
- Vehicle pricing models
- Automotive data providers
- Marketplace applications
- Recommendation engines
- Predictive analytics
Marketplace 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 For
We 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 Apply
Please send:
- Resume or LinkedIn profile
- GitHub or portfolio
- Examples of AI/automation projects
- Experience working with APIs or large datasets
- Any automotive experience
- Compensation expectations
Please 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?