y combinator jobs in Chicago

This is a remote, project-based role for mechanical engineers with hands-on experience in CAD and mechanical design. You will complete tasks spanning mechanical design, engineering analysis, technical documentation, and product development support. Work is asynchronous and assigned on a project-by-project basis, with an expected commitment of 10–20 hours...

AfterQuery is seeking experienced Insurance professionals to help train and evaluate AI systems with real-world domain judgment. This is a remote, project-based role: apply your hands-on expertise to review scenarios, label and evaluate domain-specific content, and provide clear reasoned assessments. Work is asynchronous and flexible. Why Apply •...

We are hiring for a Sales Development Representatives (SDR) and an Enterprise Lead to join our client's growing sales teams in Chicago. SDR role: The ideal candidate has 6+ months of SaaS SDR/BDR experience and is excited about building pipeline and driving new conversations. Enterprise Lead: The ideal candidate has 1-3 years of Enterprise/Strategic BDR...

AfterQuery is seeking experienced Contract Managers and Negotiators to help train and evaluate AI systems on real-world contracting work. This is a remote, project-based role: apply your hands-on expertise to review commercial agreements, assess negotiation strategy, and evaluate whether AI-generated contract language is accurate, complete, and commercially...

AfterQuery is looking for experts with experience in software engineering, computer science, or app/web development to help train and evaluate AI models. This is a remote, project-based role: qualify once through a single assessment and receive ongoing project matches spanning code review, evaluation, and original task creation. Pay ranges from $50 to...

AfterQuery is seeking Finance Experts to help train and evaluate how AI models reason about finance. Work includes writing challenging finance prompts, evaluating model responses for accuracy and sound reasoning, and spotting subtle errors like miscalculated metrics. Projects span financial modeling, valuation, accounting, corporate finance, and markets. The...

AfterQuery is seeking experienced Supply Chain professionals to help train and evaluate AI systems with real-world domain judgment. This is a remote, project-based role: apply your hands-on expertise to review scenarios, label and evaluate domain-specific content, and provide clear reasoned assessments. Work is asynchronous and flexible. Why Apply •...

AfterQuery is looking for experts with experience in software engineering, computer science, or app/web development to help train and evaluate AI models. This is a remote, project-based role: qualify once through a single assessment and receive ongoing project matches spanning code review, evaluation, and original task creation. Pay ranges from $50 to...

AfterQuery is looking for experts with experience in software engineering, computer science, or app/web development to help train and evaluate AI models. This is a remote, project-based role: qualify once through a single assessment and receive ongoing project matches spanning code review, evaluation, and original task creation. Pay ranges from $50 to...

AfterQuery is looking for experts with experience in software engineering, computer science, or app/web development to help train and evaluate AI models. This is a remote, project-based role: qualify once through a single assessment and receive ongoing project matches spanning code review, evaluation, and original task creation. Pay ranges from $50 to...

AfterQuery is looking for experts with experience in software engineering, computer science, or app/web development to help train and evaluate AI models. This is a remote, project-based role: qualify once through a single assessment and receive ongoing project matches spanning code review, evaluation, and original task creation. Pay ranges from $50 to...

AfterQuery is seeking Finance Experts to help train and evaluate how AI models reason about finance. Work includes writing challenging finance prompts, evaluating model responses for accuracy and sound reasoning, and spotting subtle errors like miscalculated metrics. Projects span financial modeling, valuation, accounting, corporate finance, and markets. The...

AfterQuery is looking for experts with experience in software engineering, computer science, or app/web development to help train and evaluate AI models. This is a remote, project-based role: qualify once through a single assessment and receive ongoing project matches spanning code review, evaluation, and original task creation. Pay ranges from $50 to...

AfterQuery is seeking Legal JD Experts to create and refine legal reasoning challenges for our AI training modules. In this remote, flexible role, you will design and evaluate legal scenarios that test the AI's ability to interpret and apply complex legal principles, ensuring that our models can navigate real-world legal issues with precision and nuance....

Why We Exist More than 80% of Americans own a car and see it as a fundamental necessity, yet the experience of owning one is stuck in the 90s. Every part of the user journey (shopping for a car, insurance, repairs, etc) is complicated, fragmented, and time-consuming, and the costs are staggering. In 2025, the cost of owning a car was more than 20% of the...

About Persistent We are an AI-led, platform-driven Digital Engineering and Enterprise Modernization partner, combining deep technical expertise and industry experience to help our clients anticipate what's next. Our offerings and proven solutions create a unique competitive advantage for our clients by giving them the power to see beyond and rise above. We...

About Persistent: We are an AI-led, platform-driven Digital Engineering and Enterprise Modernization partner, combining deep technical expertise and industry experience to help our clients anticipate what’s next. Our offerings and proven solutions create a unique competitive advantage for our clients by giving them the power to see beyond and rise above....

About Persistent: We are an AI-led, platform-driven Digital Engineering and Enterprise Modernization partner, combining deep technical expertise and industry experience to help our clients anticipate what's next. Our offerings and proven solutions create a unique competitive advantage for our clients by giving them the power to see beyond and rise above. We...

More than 80% of Americans own a car and see it as a fundamental necessity, yet the experience of owning one is stuck in the 90s. At Jerry.ai, we are building the first app to manage it all. Since launching in 2019, we’ve reached 5M+ customers, raised $240M+, scaled revenue 70X, and achieved profitability in 2024. Operating across the US and Canada brings...

Jerry is the #1 rated app for car owners. We help over 5 million people save money on insurance, repairs, and loans—all in one place. Since 2019, we’ve become one of the fastest-growing tech companies in the U.S. We are looking for an Insurance Compliance & Regulatory Senior Lead to join our Insurance Operations team. Reporting directly to our Senior...