Top Tech Jobs & Startup Jobs in Chicago, IL

Lead AI-enabled financial planning and strategic analysis, build data-backed business cases, refine unit economics, deliver executive-level insights, integrate ML into FP&A, and track KPIs to drive profitability and strategic decisions.

Develop and maintain checkers for competitive programming problems allowing multiple valid outputs, verify participant submissions, write clear C++ code, document logic, collaborate with customers, and provide feedback to improve test cases and checkers.

Build and maintain operating and cash-flow models, apply AI/ML and data techniques to automate forecasts, run sensitivity and scenario analysis, translate strategy into financial outcomes, support fundraising/M&A/pricing, and create dashboards and reports for stakeholders.

Act as the internal voice of the customer, partnering with Sales, Product, and Engineering to design and configure billing, revenue recognition, and invoicing solutions. Lead discovery with finance leaders, build demo/sandbox environments, respond to RFPs, document handoffs, and create onboarding materials while advocating customer needs to Product and Engineering.

Lead integration of AI-driven tools into tax provision, planning, and multi-jurisdictional compliance. Design ML/analytics solutions for sales and payroll tax, enhance regulatory filings, support audits, and collaborate with finance, legal, and technology teams. Monitor tax regulation changes, document AI tax models for transparency and governance, and continuously refine models for scalability, reliability, and compliance.

Provide subject-matter expertise in personal financial planning and wealth management to train and evaluate AI-driven advisory tools. Review client scenarios, give structured written feedback, translate complex financial concepts into client-friendly guidance, ensure compliance with regulatory and fiduciary standards, and contribute to improving AI recommendations for investment, retirement, estate, and debt-management planning.

Drive net-new enterprise IT services revenue by owning full sales lifecycle: prospecting, executive engagement, solution positioning, collaboration with presales/delivery, pipeline management, and closing multi-year managed services, application modernization, and digital transformation deals to meet $5M–$10M annual targets.

Provide mechanical engineering domain expertise to create and review technical content used to train AI systems: review documents, develop and assess questions/solutions, give written and oral feedback, collaborate cross-functionally, resolve complex engineering problems, and improve data quality while working independently.

Develop and support customized Acumatica ERP solutions using the Cloud xRP Platform, C#/.NET, T-SQL, APIs, workflows, dashboards, and reports. Translate business needs into technical specifications, build integrations, conduct testing, troubleshoot issues, document solutions, and collaborate with clients, analysts, project managers, and technical teams. The role also provides technical guidance, manages multiple assignments, and supports continuous improvement.

Lead Microsoft Dynamics 365 Business Central implementations from discovery through go-live, including requirements gathering, solution design, configuration, testing, training, and deployment. Advise customers, facilitate workshops, manage stakeholders, resolve functional issues, and collaborate with technical and product teams. The role also contributes to consulting methodologies, process improvements, automation, and AI-enabled implementation practices. Travel is approximately 20–25%, primarily for customer meetings and strategic project milestones.