Top Tech Jobs & Startup Jobs in Chicago, IL

Design, launch, and scale Wing's centralized corporate training function. Build strategy, select AI-driven learning tools, create adaptive learning pathways for safety, leadership, engineering, and compliance, deliver training, partner with cross-functional teams, and evolve the function from individual contributor work to a small team.

Manage the AHS accounting department, oversee month-end close, general ledger maintenance, balance sheet reconciliations, financial reporting, budget variance analysis, and chart of accounts. Develop accounting policies, support annual budgeting, ensure internal controls to prevent fraud, and work closely with the Controller to ensure accurate financial statements for all entities.

Lead Net at Work's internal IT organization, ensuring reliability, security, scalability, and performance across applications, infrastructure, cloud, and cybersecurity. Oversee application rollouts, SDLC practices, operations, vendor relationships, budgeting, and acquisition due diligence. Partner with executives and business leaders to align technology roadmaps, governance, and service delivery while building a service-oriented, high-performing IT team.

Own end-to-end onboarding of enterprise customers onto the TPRM platform: gather requirements, configure workflows, build API integrations and automation, handle data migration, run discovery and training, document solutions, and manage multiple implementations to go-live.

Own strategy, roadmap, and delivery for first-party and third-party risk management products. Define features across the risk lifecycle, conduct customer discovery, translate domain requirements into specs, collaborate with engineering/design/QA, monitor metrics, and partner with go-to-market teams to drive adoption.

Build and ship first-party risk management features end-to-end: risk registers, risk scoring, control testing, monitoring, and framework integrations. Implement backend services/APIs and React/TypeScript front-end components, collaborate with product/design/QA, and ensure data integrity and test coverage in a compliance-focused SaaS product.

Lead and develop a team of quota-carrying sellers to meet team revenue targets. Own pipeline health, forecasting, territory design, playbook creation, coaching, and performance management. Partner cross-functionally to remove blockers, join client meetings, handle escalations, and represent Chicory externally. Deliver data-informed forecasts and build repeatable sales processes while fostering team culture and retention.

Build and maintain production-grade data pipelines and ELT processes using Python, SQL, Airflow, and dbt within AWS. Design optimized schemas in PostgreSQL and Redshift, leverage AI/LLMs to improve development, automation, testing, and data quality, and scale infrastructure for large healthcare datasets.

Handle inbound client calls and emails for the Rental Team, process endorsements and bind requests, maintain accurate policy records, and resolve system issues while ensuring compliance and excellent customer service.

Support compliance monitoring, testing, and branch audits for acquired firms during integration. Conduct risk assessments, audits, and branch exams; identify trends, document workpapers, track remediation action plans, assist policy development, and report to Compliance leadership while staying current on regulatory developments.

Design, implement, and administer the firm's enhanced-risk monitoring and supervision framework for clients, employees, advisors, and business practices. Develop risk-scoring and high-risk criteria, oversee enhanced due diligence, manage heightened supervision plans, perform risk assessments, produce dashboards and reports, and support regulatory readiness and audit documentation.

Support FP&A for a dental practice management SaaS: build financial models, forecast ARR/MRR, automate reporting with BI and AI, analyze practice usage and pricing, integrate SAP/Salesforce data, and deliver executive dashboards and insights for product, sales, and operations.

Lead client success for large employer clients on the West Coast. Deliver data-driven value stories, support renewals and upsells with financial models, build executive-level relationships, define and hit KPIs, resolve client issues cross-functionally, and travel ~25% to maintain strong partnerships and drive retention and growth.