Top Tech Jobs & Startup Jobs in Chicago, IL

Design, build, and maintain CI/CD pipelines, deployment tooling, and release systems. Improve build/deploy speed, troubleshoot failures, partner with product teams, and coach engineers to reduce delivery friction.

Lead technical strategy and execution for build, test, release, and deployment systems. Drive initiatives to improve developer productivity, deployment safety, and platform reliability. Coordinate cross-team projects and migrations, contribute high-impact code, coach engineers, and lead incident response and resilience improvements for shared engineering systems.

As a Lead Machine Learning Engineer at Root, you'll build scalable ML systems, partner with data scientists, and improve operational practices for customer lifetime value modeling.

Lead a multidisciplinary team to design, deploy, and optimize ML-driven bidding systems and measurement for a nine-figure marketing budget. Drive experimentation, partner strategy, media-mix optimization, and end-to-end measurement while aligning Marketing, Analytics, Engineering, and Product to improve marketing ROI and scale performance.

Lead vision, strategy, and roadmap for pricing platforms, owning internal Rating Plan Manager and tooling to speed model deployment, improve workflow reliability and observability, enable self-service experimentation, and support regulatory/state-level pricing needs through cross-functional collaboration.

Drive growth in the Independent Agent channel by outbound prospecting, onboarding new agents, delivering product training, conducting business reviews, driving agent engagement, and collaborating with internal teams to improve agent experience and product adoption.

The Principal Software Engineer will lead technical initiatives, align cross-functional teams, establish standards, and guide multiple engineering teams towards strategic objectives, driving large-scale improvements in business outcomes.

Own and scale Root's largest enterprise partnerships (OEMs, financial institutions, dealer groups). Drive account strategy, manage a $100M+ pipeline, identify and close new business, lead executive negotiations and contract execution, coordinate cross-functional launches, monitor partnership health, and influence product and commercial strategy to deliver growth.

Lead and scale Root's Financial Institutions vertical by owning the full partnership lifecycle: market strategy, enterprise pipeline, C-suite negotiations, implementation, executive governance, and long-term expansion. Build executive relationships with banks, credit unions, fintechs, and payment providers; structure commercial models using embedded insurance and SaaS capabilities; partner cross-functionally to prioritize product investments; and drive revenue, profitability, and forecasting.

Lead data science for Root's digital partnerships channel, managing a team to drive growth, profitability, experimentation, forecasting, optimization, and measurement. Partner with cross-functional teams to improve acquisition economics, influence product and technical roadmaps, deliver executive reporting, and establish scalable operating processes.