AI Software Engineer – Automotive Deal Sourcing & Marketplace Automation

About the role

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?