Top Tech Jobs & Startup Jobs in Chicago, IL

As a Senior Design Engineer at Benepass, you will build and evolve the design system, collaborate with Design and Product teams, and drive high-quality frontend development while improving developer experience.

The Staff Software Engineer will design and operate high-integrity financial systems including ledgering, transaction processing, and money movement while ensuring system correctness and resilience.

Design, build, and maintain scalable ETL/data pipelines across distributed systems. Ensure data quality, integrity, security, and high availability. Monitor and optimize pipeline performance, perform root cause analysis, document systems, collaborate with global teams, and participate in on-call rotations to support production data systems.

The Channel Partner Director will lead partner recruitment, develop joint business plans, manage revenue growth, and optimize partner performance to achieve revenue targets. Responsibilities include overseeing partnerships, tracking metrics, and collaborating cross-functionally to enhance integration and sales strategies.

Lead a Front End Infrastructure squad that builds and maintains mobile platform systems (CI/CD, shared libraries, observability, analytics, experimentation, design systems). Balance people management and hands-on technical guidance across React Native, iOS, Android, and developer tooling; drive roadmap, architecture, hiring, cross-team collaboration, and platform health metrics.

Lead Reddit organic marketing and SEO/AEO programs, develop playbooks for AI-driven visibility (e.g., ChatGPT), execute data-driven campaigns, and provide detailed analytics and reporting to meet client KPIs.

Serve as first-line support for Relocity's web and mobile platform: manage Intercom tickets, troubleshoot and reproduce issues, escalate to Product/Engineering, maintain documentation, identify trends, and support product adoption while contributing to knowledge base and process improvements.

Own end-to-end onboarding and activation for new B2B SaaS customers, driving time-to-first-purchase and GMV within 60–90 days by project-managing implementations, removing friction, collaborating cross-functionally, building scalable playbooks, and measuring activation metrics.

Lead the creation and operation of a Customer Success function to drive onboarding, adoption, retention, and expansion. Build playbooks, instrument CS metrics (TTV, NRR, health score, churn), manage tiered engagement models, present business reviews to executives, maintain knowledge resources, and coordinate with Product, Support, and Sales to reduce churn and grow customer revenue.

As a Staff AI Engineer, you will design and implement AI-powered automation for internal departments, manage the full project lifecycle, and enhance various processes across CargoSprint, focusing on business impact and collaboration.

Provide guidance and counsel to leadership on complex labor and employee relations matters including CBA interpretation, investigations, grievance administration, conflict resolution, performance and termination management. Partner with union leadership, internal/external counsel, and stakeholders to reduce risk, conduct root-cause analysis, deliver training, and support mediations, arbitrations, and legal proceedings.

Mainstay seeks to connect with potential candidates for future roles across various fields including engineering, analytics, product, sales, and operations.