Top Tech Jobs & Startup Jobs in Chicago, IL

Lead design and delivery of a unified, real-time billing platform that embeds AI/ML to automate reconciliations, detect anomalies, enable predictive insights, and create autonomous finance workflows across global billing operations.

Lead applied AI research to design and prototype Transformer-based Payment Foundation Models and generative AI solutions for fintech use cases. Drive self-supervised pre-training, fine-tuning, model optimization, benchmarking, and evaluation; collaborate cross-functionally to transition prototypes to production and ensure responsible, secure AI deployment while mentoring engineering teams.

Lead and grow the Mobility Mobile Engineering organization to deliver high-quality iOS and Android apps. Define technical vision and roadmap, partner with cross-functional teams, improve engineering processes and metrics, drive delivery of large initiatives, hire and develop managers and engineers, and ensure mobile security, reliability, and product-aligned execution.

Architect, build, and deploy production-grade AI/ML platforms and LLM/RAG solutions. Lead system design, CI/CD and Terraform-based IaC, ensure reliability and monitoring, mentor engineers, run incident response, and prototype emerging AI technologies.

Lead global engineering teams to design, build, and operate cloud-native payments platforms. Drive AI-native engineering practices, platform modernization, scalable microservices, and predictable software delivery. Partner with Product, Architecture, Security, and Commercial teams to deliver payment orchestration, processing, treasury, and API-first capabilities while transforming engineering culture and productivity.

Sell WEX telematics solutions to small and mid-sized fleets by managing a pipeline, negotiating and closing deals, upselling, forecasting MRR in Salesforce, collaborating with customer success and partners, and mentoring junior sales team members.

Lead architecture and roadmap for a company-wide data lakehouse platform. Build platform-as-product components (SDKs, CLIs, control planes), optimize distributed compute/storage, prototype performance R&D, ensure compliance-by-design (lineage, PII masking, access control), enable real-time AI data ingestion, drive engineering standards, and mentor cross-functional teams.