Top Tech Jobs & Startup Jobs in Chicago, IL

Lead commercial and technology contracting, negotiating SaaS, API, data, AI, vendor, carrier, and partnership agreements. Advise on AI, privacy, data, IP, and technology risks; develop contract playbooks, templates, workflows, and training; oversee legal AI and contract management tools; and manage, mentor, and develop a contracts team. Support commercial disputes, litigation, and corporate projects as needed.

Develop and scale strategic partnerships with SMBs by sourcing opportunities, negotiating agreements, positioning products, and managing implementations through growth. The role owns partnership pipeline development, evaluates strategic fit, coordinates cross-functional teams including Product, Engineering, Legal, Finance, and Marketing, monitors competitive activity, and communicates findings to leadership. Success requires strong negotiation, communication, project execution, attention to detail, and the ability to navigate ambiguity in a fast-paced environment.

Build and deploy machine learning models that personalize insurance products, analyze product data, design experiments, and measure model impact. The role owns the full data science lifecycle, including data wrangling, production coding, model monitoring, retraining, and experimentation. Responsibilities also include cross-functional collaboration, code reviews, mentoring data scientists, and improving platform practices.

Sources, evaluates, negotiates, and secures strategic partnerships that expand The Zebra’s reach and revenue. Responsibilities include building partnership pipelines, analyzing deal value, managing contracts, coordinating implementation across teams, researching industry trends, developing sales materials, collaborating with Product, and strengthening brand awareness. The role requires executive-level relationship building, presentations, cross-functional influence, and travel of 25% or more.

Lead and mentor a software engineering team, provide technical guidance, drive architecture and engineering excellence, manage sprint execution, collaborate on product roadmaps, ensure scalable and reliable systems, foster continuous improvement, and support recruiting and onboarding. The role requires balancing technical strategy with business impact while developing high-performing engineers.

Own the HR systems ecosystem, including configuration, workflows, integrations, automation, data integrity, reporting, compliance controls, and Jira intake. Lead system implementations, upgrades, redesigns, documentation, and training while partnering across People Operations, IT, Compliance, Security, Finance, Legal, and vendors. Apply AI and automation to reduce manual work and improve employee support.

Leads and develops product, marketing, and data analysts while overseeing analytics strategy, prioritization, technical standards, experimentation, reporting, and data quality. Partners with Product, Marketing, Finance, Engineering, and recruiting to deliver trusted insights, scalable self-service analytics, and team growth. Requires strong SQL and Python skills, modern data-tool experience, analytics leadership, stakeholder communication, and at least five years in data roles with two years managing teams.

Leads quality strategy and automated testing across functional, integration, and end-to-end applications. Owns test frameworks and infrastructure, integrates testing into CI/CD pipelines, plans release testing with Engineering and Product, tracks quality metrics, improves defect prevention, contributes to tooling standards, and mentors junior quality engineers.