Top Tech Jobs & Startup Jobs in Chicago, IL

Own end-to-end BSA/AML investigations for cannabis banking clients, including alert monitoring, risk assessments, marijuana-related SAR filings, transaction-monitoring rule calibration, CRB onboarding, license verification, beneficial ownership analysis, account reviews, and support for audits and regulatory examinations. The role requires expertise in FinCEN guidance, state cannabis regulations, BaaS compliance models, AML platforms, and cannabis banking typologies.

Leads the payments and banking product roadmap for a regulated cannabis fintech platform. Owns product vision, KPIs, market research, compliance requirements, partner integrations, prioritization, and customer adoption. Collaborates with executives, financial institutions, fintech providers, designers, engineers, marketing, and account teams to launch embedded payment, banking, liquidity, and credit capabilities.

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.

Lead product strategy, discovery, and execution for LeafLink's marketplace and financial services. Partner with Design, Engineering, Data, Operations, and Commercial teams to define roadmaps, validate solutions, ship customer-facing B2B products, measure outcomes, and iterate using customer research and analytics.

Lead the entire engineering organization: set technical vision, architecture, and operating model; recruit and develop managers; own delivery, reliability, security (SOC 2), budgeting, and metrics; improve velocity while reducing technical debt; partner with product and execs to drive roadmap and org-scale decisions.

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.