Top Tech Jobs & Startup Jobs in Chicago, IL

Lead and mentor a global SRE team while overseeing incident response, system health, availability, performance, monitoring, logging, automation, and capacity management. Develop reliability tooling, improve observability, support on-call operations, and partner with engineering and product teams on reliability-focused initiatives. The role also involves project leadership, compliance adherence, and proactive reduction of operational toil through automation and engineering practices.

Leads commercial legal support for Mobility and Payments across the Americas. Advises executives and cross-functional teams, manages legal professionals and outside counsel, and drafts and negotiates complex commercial agreements. Supports product development from inception through launch, maintains product terms, manages risks and disputes, and contributes to M&A, RFPs, marketing review, process improvements, templates, and negotiation playbooks.

Partners with Technology and Digital leadership on budgeting, forecasting, reporting, and investment decisions. Manages close activities, accruals, reconciliations, SOX controls, and financial data integrity. Consolidates technology spending data, improves capital planning, and automates financial processes. Provides actionable analysis of cost drivers and resource investments while communicating insights to senior stakeholders and collaborating across Finance, Technology, and Product teams.

Lead modernization of complex SQL Server stored procedures and design AI-native data infrastructure. Responsibilities include domain-driven data architecture, event-driven patterns, vector databases, embedding pipelines, semantic models, knowledge graphs, RAG evaluation, multi-platform data solutions, governance, and AI-assisted database tooling. The role partners across engineering and AI/ML teams, establishes reference architectures, mentors engineers, and contributes to enterprise data standards.

Lead the global Risk Operations initiative portfolio across Collections, Billing, Treasury, and related financial operations. Identify strategic initiatives, align projects with risk and customer experience goals, coordinate resources and timelines, oversee technology roadmaps, manage risks, and provide executive reporting. Facilitate cross-functional collaboration among technical, legal, audit, risk, sales, and account management teams while ensuring compliance and operational control integrity.

Support Corporate Payments commercial and transactional work: draft/revise NDAs and revenue-generating contracts, manage contract lifecycle in Malbek, handle matter intake in Xakia, assist attorneys with transaction documents, coordinate approvals/execution, and collaborate with Finance, Compliance, and Risk.

Leads architecture and hands-on development of WEX’s semantic data platform and Data-as-a-Service capabilities. Builds reusable semantic business objects, metadata and ontology frameworks, knowledge graphs, APIs, governance, lineage, quality, and data contracts. Solves distributed-systems and scalability challenges while enabling AI and agentic applications to use trusted enterprise data. Partners across engineering, product, analytics, risk, finance, and business teams; influences technical standards, drives adoption, mentors engineers, and remains involved in implementation.

Build and own Snowflake data models and dbt pipelines for a Customer Data Platform supporting marketing segmentation and customer journeys. Integrate complex source systems, manage data architecture and governance, conduct data discovery, and translate business rules into scalable solutions. Collaborate with engineering, analytics, product, and business stakeholders; lead technical workshops; mentor junior engineers; and implement automated data quality testing, CI/CD workflows, and AI-augmented engineering practices.

Supports WEX Mobility’s commercial and transactional legal work by drafting, redlining, reviewing, routing, executing, and managing customer and revenue-generating contracts. Maintains contract and matter workflows in Malbek and Xakia, coordinates approvals with attorneys and cross-functional teams, handles legal notices and administrative matters, migrates legacy contracts, and supports compliance documentation and strategic projects.

Manage full-cycle recruiting for Sales, Marketing, and Operations roles, from intake through onboarding. Responsibilities include sourcing passive candidates, screening and interviewing applicants, advising hiring managers, negotiating offers, maintaining talent pipelines, tracking recruiting metrics, ensuring EEO and compliance adherence, and improving recruitment processes using Workday ATS and Phenom CRM.