Top Tech Jobs & Startup Jobs in Chicago, IL

Partner with attorneys to design, build, deploy, and maintain AI-enabled legal workflows (prompting, RAG, templates, evaluations). Provide training, change management, governance-aligned guardrails, monitor adoption and performance, and iterate on workflows with cross-functional teams.

Lead technical discovery with federal customers to define requirements and design secure, compliant cloud-native architectures. Build POCs/MVPs, produce architecture and deployment documentation, integrate third-party tools, guide implementations, and align sales, engineering, and product teams to deliver AI-driven knowledge management solutions for government environments.

Provide commercial transactional legal support for large, complex merchant and partner deals globally. Negotiate and draft multinational agreements, advise sales and cross-functional teams on payments, licensing, and regulatory risk, manage deal closings, ensure compliance, escalate high-stakes issues, and develop risk management frameworks to protect PayPal's legal interests.

Lead visual storytelling across brand, digital product, motion, and environmental experiences. Collaborate with multidisciplinary teams to translate research and strategy into high-fidelity deliverables, prototypes, and brand systems. Advocate for craft excellence, contribute to client-facing presentations, and iterate across exploratory and polished work to communicate user stories and strategic intent.

Supports a global Microsoft Dynamics 365 ERP integration strategy by configuring Finance & Operations and Customer Engagement modules, establishing legal entities, defining business requirements, and resolving system and data issues. Leads functional testing, UAT, deployment, test automation, quality assurance, and data migration validation. Collaborates with legal, finance, operations, and technical teams to improve business processes, automate workflows, close process gaps, and ensure accurate, effective ERP implementations.

Manage post-sale customer lifecycle for AEC clients: lead onboarding, conduct health checks, resolve escalations, advocate for customers internally, and identify upsell and renewal opportunities.

Design, build, test, and maintain inbound/outbound Workday HCM and Finance integrations (Studio, Core Connectors, EIBs, Web Services/REST/SOAP). Lead technical lifecycle from requirements to deployment, create Workday reports and calculated fields, handle XML/XSLT, support security/networking for integrations, prepare documentation, and provide testing and post-production support.

Analyzes business processes, data quality, and datasets to identify AI and automation opportunities. Translates business requirements into AI/ML use cases, collaborates on model development, evaluates model performance, and creates dashboards and reports. The role monitors AI solutions, researches emerging technologies, and supports governance, compliance, responsible AI, and prompt engineering initiatives while partnering with data scientists, engineers, product teams, and business stakeholders.

Develop and maintain scalable Snowflake data warehouses, ETL/ELT pipelines, data models, and integrations across cloud and on-premises sources. Optimize queries, clustering, partitioning, and warehouse performance; implement transformations using SQL, stored procedures, and Snowpark. Monitor data quality, governance, security, deployments, and production issues. Collaborate with engineers, architects, analysts, and business stakeholders while automating workflows and contributing to data architecture and best practices.

Design, develop, and maintain automated testing solutions for customer-facing applications and web services. Build test frameworks, integrate tests into CI/CD pipelines, and improve coverage, reliability, security, and release quality. Develop front-end and web-service automation using Groovy/Geb and Java/HttpClient, troubleshoot application issues, participate in code and test reviews, and collaborate with Agile development teams throughout the software lifecycle.

Operate as a founder on client projects: own strategy and execution, present AI roadmaps, design and build AI systems (vision pipelines, document extraction, recommendation engines), ship solutions across varying stacks, communicate technical tradeoffs to non-technical stakeholders, and adapt quickly to different industries and tools.

Manage a portfolio of homeowner associations: attend board meetings, perform inspections, prepare meeting and financial packages, supervise vendors and staff, oversee ARB and AP processes, maintain records, and ensure compliance with management agreements and statutes.