Top Tech Jobs & Startup Jobs in Chicago, IL

Owns the strategy, roadmap, backlog, and delivery of Caterpillar’s Unified Catalog and PIM capabilities. Responsibilities include product data modeling, taxonomy, governance, integrations, data quality, onboarding, and supporting search, filtering, localization, and digital product experiences. The role partners with engineering, CMS, analytics, marketing, dealers, and business stakeholders to improve catalog scalability, completeness, accuracy, and time-to-market.

Partner with application teams to identify, prioritize, and remediate security findings from automated and manual testing, penetration tests, and bug bounty programs. Provide secure development guidance, manage application security testing tools such as CodeQL and Rapid7, coordinate penetration testing, track defects, and improve security maturity through scorecards and corrective-action learning.

Leads enterprise marketing technology architecture and multi-year roadmaps across content, digital experience, PIM, commerce, analytics, personalization, identity, and omnichannel platforms. Designs application, data, integration, and infrastructure architectures; guides platform strategy, governance, security, privacy, and lifecycle management. Partners with marketing, product, data, security, and engineering teams, evaluates technologies, leads architecture reviews, resolves complex design issues, directs delivery partners, and mentors technical talent while aligning investments to measurable business outcomes.

Owns the product vision, backlog, priorities, feature decisions, and sprint outcomes for Caterpillar’s cloud platform services. Partners with engineering teams and stakeholders to define requirements, acceptance criteria, API contracts, and releases. Leads Scrum ceremonies, defect prioritization, and customer engagement while supporting AI-assisted development and AWS cloud architecture decisions. Requires strong software development knowledge, including Java, REST APIs, databases, AWS, Agile tools, and spec-driven development.

Develops accurate, actionable business insights for dealers and product teams to support parts and service growth. The role analyzes large datasets, identifies and resolves data-quality issues, measures insight effectiveness, translates findings into recommendations, supports training and adoption, and coordinates with product management and stakeholders on insight quality, reliability, usability, releases, and change control.

Develop and deploy generative AI assistants, agents, tooling, and software using Python and cloud technologies. Build CI/CD pipelines, deploy AWS services with CloudFormation, and use frameworks including LangChain, LangGraph, Semantic Kernel, and CrewAI. Develop FastAPI services, collaborate with data scientists to productionize analytics solutions, and support machine learning pipelines with Apache Airflow. Serve as a technical lead on complex projects and contribute to software architecture, testing, scalability, and technical documentation.

Provide production support and platform stability for Caterpillar’s AWS-based autonomy platform. Manage incidents from triage through resolution, coordinate technical fixes across engineering and support teams, conduct root cause analysis, maintain operational runbooks, monitor cloud services, and improve reliability and operational readiness. The role also supports automation, API troubleshooting, CI/CD issue tracing, knowledge transfer, and stakeholder communication.

Lead advanced digital and rental analytics using GA4, BigQuery, Python, and SQL. Analyze clickstream data, customer journeys, conversion funnels, attribution, and site performance to improve revenue and customer growth. Define KPIs, develop analytics roadmaps, apply statistical and machine learning methods, establish data governance, and translate insights into recommendations. Collaborate with senior leaders, product owners, strategy teams, and technical stakeholders while supporting scalable measurement solutions and data-driven product development.

Leads a software system integration testing team focused on APIs, services, data pipelines, and system interfaces. Owns test strategy, automation frameworks, quality standards, test environments, schedules, release readiness, defect triage, and quality reporting. Partners with engineering, product, and architecture teams while hiring, mentoring, and developing test engineers. Drives CI/CD test integration, improves test coverage, reduces flaky tests, and ensures compliance with security, safety, and industry standards.

Leads change management and dealer training for Caterpillar’s Microsoft Dynamics 365 ERP transformation. Responsibilities include managing project activities, schedules, risks, dependencies, stakeholder communications, training strategy, change frameworks, requirements gathering, adoption metrics, and dashboard reporting. The role coordinates product feature intake, supports agile delivery, educates global users, and drives adoption across dealers and internal teams.