Top Tech Jobs & Startup Jobs in Chicago, IL

Lead institutional customer AML/KYC onboarding, including escalations, account decisions, customer RFIs, and risk-based due diligence. Ensure procedures comply with BMA, FinCEN, FATF, OFAC, and global requirements. Improve onboarding policies, timelines, data quality, automation, and customer experience while monitoring KPIs and reporting to senior leadership. Collaborate cross-functionally with Engineering and lead onboarding strategy in a regulated fintech environment.

Senior Legal Counsel will advise on healthcare regulatory, corporate, commercial, privacy, employment, litigation, product, and AI-related matters. The role will negotiate contracts, develop legal templates and processes, guide Medicaid and Medicare compliance, support care delivery and workforce policies, manage outside counsel, and partner with clinical, operational, product, and business teams to identify risks and enable responsible growth.

The VP of Finance will build financial foundations, own FP&A, provide decision support, upgrade reporting, and develop the finance team.

Own Pacaso’s lifecycle marketing strategy and execution across reactivation, prospect nurture, and owner communications. Build and manage Iterable journeys, segmentation, personalization, catalogs, templates, deliverability, and email, SMS, and push channels. Connect lifecycle systems with CRM and data infrastructure, measure conversion and revenue impact, and report results to leadership. Partner with Sales, brand, creative, analytics, and owner experience teams while using AI to improve campaign speed and performance.

Lead quality assurance for storage and filesystem features, designing test strategies, executing system, stress, regression, and cross-functional testing, and developing automation. Collaborate with developers, tools teams, and customer support to improve testability, reproduce issues, and debug defects. The role requires expertise in NFS, SMB, NAS filesystems, Linux, Windows, VMware, shell scripting, Python, packet capture, test infrastructure, and release management.

Manage development, planning, marketing and delivery of military children and residential camp programs. Supervise staff and volunteers, ensure participant inclusion, oversee budgets, billing, marketing, grants, and program materials. Recruit and train staff, evaluate program outcomes, and maintain required records and compliance.

Lead the architecture and development of a multi-RAT Open RAN digital twin supporting LTE and 5G NR simulation. Integrate production MAC and scheduler software with PHY, channel, UE, traffic, mobility, interference, and network models. Build fidelity tiers, AI/ML evaluation pipelines, reproducible experiments, calibration and validation practices, automated testing, and CI/CD workflows. Improve simulation scalability and reliability while collaborating across wireless, PHY, AI/ML, software, and lab-validation teams.

Support accounts payable, state sales tax filings and registrations, broader tax compliance, and monthly close activities. Responsibilities include invoice review, payment processing, reconciliations, accruals, amortization, and coordinating with external tax advisors. The role also identifies opportunities to improve accounting processes, controls, and workflows in a fast-growing, remote technology company.

Build and optimize Databricks Lakehouse architectures and scalable ETL/ELT pipelines using Spark and Delta Lake across AWS, Azure, and GCP. Tune performance and cloud costs, integrate MLflow for AI model operationalization, and implement CI/CD and Infrastructure-as-Code deployments. Enforce governance, security, and compliance through Unity Catalog. Partner with architects, data scientists, engineers, and clients to deliver production-ready AI solutions and documentation.

Provides customer support through phone, chat, and email for health insurance shoppers and existing customers. Assists with online insurance navigation, quotes, administrative questions, and billing issues while documenting interactions in support systems. The role requires high-volume multitasking, strong communication, customer service or sales experience, and availability during weekday Central Time hours. It is fully remote and includes opportunities to suggest process and product improvements.