Top Tech Jobs & Startup Jobs in Chicago, IL

Handle high-volume cash and electronic payment processing (wires, ACH), reconcile transactions and general ledger entries, investigate and resolve exceptions, ensure BSA/AML and OFAC compliance, support audits and month/quarter/year-end reporting, and recommend process improvements to reduce errors.

Lead risk and compliance activities for a high-risk banking environment: prepare for audits and regulatory exams, draft policies and governance, evaluate internal controls, run risk assessments and gap analyses, maintain training, monitor regulatory changes, and produce KRI/KPI Board-level reporting.

Contract operations specialist responsible for high-volume cash intake, wire and ACH processing, reconciliation, exception investigation, compliance with BSA/AML and OFAC, audit support, and process improvement to maintain accurate client account transactions.

Provide in-house corporate legal support for commercial, regulatory, and governance matters at a fast-growing cannabis SaaS/fintech platform. Draft, review, and negotiate commercial, banking, fintech, data licensing, and technology agreements; advise product, engineering, finance, and GTM teams on compliance, privacy, and risk; build contract templates and playbooks; support board and investor governance; manage outside counsel and regulatory matters.

Support cross-functional projects to improve operational workflows, perform market and ad-hoc analyses, maintain SOPs and reporting, deep-dive into data to surface trends and recommendations, and clean up CRM and reporting infrastructure. Prepare biweekly operational performance reports and lead initiatives across Sales, Marketing, Product, Operations, Policy, and Finance.

Manage a book of cannabis brand clients to drive adoption, retention, and revenue through LeafLink's marketplace and financial solutions. Provide strategic guidance, training, cross-sell/upsell, track product issues, use Salesforce for account activity, and collaborate with Sales, Product, and Support to improve customer outcomes.

Lead and mentor a team building LeafLink’s eCommerce marketplace. Provide technical leadership, set architecture and delivery plans, coordinate cross-team dependencies, manage incidents, recruit talent, and balance product delivery with platform health, scalability, security, and developer productivity.

Design, build, and maintain scalable backend services and APIs for commerce workflows using Python/Django. Improve reliability, performance, and observability, operate AWS deployments, work with PostgreSQL and event-driven architectures (SNS/SQS), modernize legacy systems, and support CI/CD, testing, and production troubleshooting.

Lead end-to-end BSA/AML investigations for cannabis clients, conduct due diligence and ongoing monitoring, prepare marijuana-related SARs per FinCEN MRB guidance, calibrate transaction monitoring rules, administer onboarding and license/beneficial ownership reviews, and support bank regulatory examinations and OFAC/PEP screening.

Lead design and scaling of the data platform and analytics pipelines. Build and maintain ETL/ELT workflows, integrations, serverless data services, and reliable data models. Mentor teammates, improve automation, observability, and data governance to support analytics and operational insights.