Top Tech Jobs & Startup Jobs in Chicago, IL

Lead and support implementations, upgrades, and configuration of Workday HCM modules. Gather and analyze HR requirements, run workshops and end-user training, troubleshoot Workday issues, and collaborate with developers and project managers to optimize HR processes and adopt Workday best practices.

Implement, maintain, and support Workday integrations and configurations. Design and manage inbound/outbound EIBs, DT XSLT transformations, core connectors (PECI/WECI), Cloud Connect, report calculated fields, and Workday Studio tasks to ensure reliable data exchange and reporting.

Manage and optimize ERP environments and multi-module integrations, evaluate and apply software releases, perform advanced SQL/database troubleshooting, identify system improvements, and serve as Salesforce Data Cloud admin handling data integration, modeling, quality, governance, and deployments while training and supporting users.

Lead hands-on administration and optimization of enterprise database platforms (SQL Server, MongoDB, MySQL/MariaDB, PostgreSQL). Manage installs, upgrades, HA/DR, performance tuning, security, automation, monitoring, and capacity planning. Drive incident resolution, cloud modernization efforts, and mentor teams on database best practices.

Own the design, development, maintenance, and performance of Microsoft Fabric data pipelines, centralized semantic models, DAX measures, and documentation. Ensure data quality, consistency, and trusted marketing metrics across sources. Partner with data engineering and BI teams on deployments and production issues, investigate model discrepancies, perform analytical work, mentor apprentices, and contribute to applied AI initiatives.

Set the technical direction for machine learning at Payabli by maturing production risk models and launching new models across the payments lifecycle. Establish experimentation, monitoring, drift detection, benchmarking, retraining, and incident-response foundations. Translate payments challenges into modeling opportunities, connect model performance to business outcomes, influence the ML roadmap, and mentor engineers while partnering with product, engineering, and risk operations.

Own the architecture and reliability of Payabli’s core payments infrastructure, including exactly-once payment execution, APIs, multi-rail orchestration, batching, funding, reconciliation, ledgering, observability, and failover. As the founding Payments Core engineer and senior individual contributor, establish technical standards, influence architecture, set hiring criteria, and build systems capable of processing high-volume money movement accurately and reliably.

Build agentic LLM systems that acquire, clean, validate, curate, and document large-scale biomedical datasets for multimodal model training. Develop reliable agent architectures, tooling, evaluation harnesses, quality-control workflows, and reproducible data pipelines. Collaborate with ML scientists, monitor distributed production pipelines, diagnose failures, and implement secure sandboxed execution with restricted access and audit logging.

Serve as the CEO's strategic and operational right hand at an AI LegalTech startup: prepare executive/board/investor materials, build financial models and decks, contribute litigation expertise to product content, validate LLM-generated analyses, drive cross-functional execution, manage company operations (recruiting, vendor administration, OKRs), represent the CEO, and handle special projects across finance, legal, and partnerships.

Owns the product backlog and translates user needs into JIRA tickets, user stories, and acceptance criteria. Partners with Product Management, Engineering, QA, and cross-functional stakeholders on prioritization, release planning, testing, and delivery. Monitors feature adoption, gathers feedback, advocates for end users, and supports business cases and ROI analysis. The role requires understanding healthcare workflows and facilitating communication among technical and business teams.

Own quality engineering for high-throughput payment systems by architecting automated regression, performance, stress, and load testing. Build emulators for external payment systems, integrate quality gates into CI/CD pipelines, validate microservices, event-driven architectures, and databases, and use Prometheus and Grafana for observability. Apply AI-assisted testing, synthetic data generation, and edge-case analysis while mentoring engineers and preventing incidents through telemetry-driven testing and post-mortems.

Own quality engineering for high-throughput payment systems by designing automated regression suites, performance and load tests, quality gates, external-system emulators, observability-driven test environments, and AI-assisted testing workflows. Partner with feature teams and product leaders to improve reliability, scalability, security, and transactional accuracy. Mentor engineers, support incident prevention, and embed automated validation throughout the software development lifecycle.

Design secure, scalable payment infrastructure solutions for prospective and existing customers. Lead technical discovery, map complex payment flows, create architectures, demos, proposals, proofs of concept, and implementation handoffs. Advise on tokenization, PCI scope reduction, processor connectivity, payment portability, resiliency, and compliance. Partner with Sales, Account Management, Product, Engineering, and customer technical teams, provide launch oversight, influence product strategy, and develop reusable integration assets and reference architectures.

Design, develop and support cloud applications using Cloud Foundry and Node.js. Apply object-oriented design and SQL (HANA). Work with APIs and eventing, use VS Code. Prefer SAP CAP/BTP and SAP experience. Collaborate in agile/SCRUM teams, communicate effectively, take ownership, and ensure high quality.

Senior full-stack developer to build scalable SAP BTP applications using Node.js, CAPM, and SAP UI5/Fiori; integrate with S/4HANA and third-party systems; optimize performance, ensure secure deployments, and follow Agile practices.

Build and maintain large-scale data processing pipelines using Apache Spark (PySpark/Scala) and Python. Design ETL workflows, implement distributed data processing, use version control (Git), and work with cloud platforms (GCP/AWS/Azure).

Provides high-level executive support to the CEO and leadership team, managing complex calendars, travel, meetings, confidential matters, and follow-through. Writes and edits executive and company-wide communications, coordinates all-hands and leadership events, prepares Board materials, and supports change communications. Improves executive-office workflows using Microsoft 365, AI tools, templates, trackers, and repeatable processes.

Lead and oversee volunteer HR operations: supervise/train HROs, manage recruiting and onboarding via Dover ATS, maintain HR documentation and systems, run meetings and strategic HR initiatives, support Executive Director on DEI and people strategy, and cover day-to-day volunteer HR duties.

Design and launch interactive podcast content (quizzes, polls, listener challenges), integrate elements with hosts, track engagement metrics, experiment with tools, and improve audience interaction.

Volunteer WordPress Developer to migrate and maintain a content library, build new features, and create custom themes, plugins, and widgets. Work remotely for ~5+ hours/week, attend weekly meetings, and respond within 24 hours to support an active nonprofit volunteer team.