Top Tech Jobs & Startup Jobs in Chicago, IL

Lead discovery and build internal AI agents and automations end-to-end: map workflows across teams, prototype LLM-powered agents, define specs, quality guardrails, and observability, drive engineering delivery and adoption, and set roadmap for internal AI platform (Rockie).

Review account activity and approve or escalate payment requests using AI-assisted analysis. Detect suspicious activity and fraud patterns, implement regulatory requirements, recommend process improvements, document procedures, and collaborate cross-functionally to balance compliance, user experience, and scalable growth.

As an Engineering Manager, you'll lead and develop an engineering team, ensuring technical quality, fostering growth, and guiding product initiatives, while utilizing AI effectively.

The Senior Product Manager will lead the Prepaid Cards team, managing cardholder journeys, product roadmap, and collaborating across technical partners while ensuring effective solutions and communication in a remote work environment.

Lead Tremendous's 17-person marketing org across demand generation, product and corporate marketing, and brand. Own pipeline generation, team development, data-driven experimentation, AI integration, and contribute to company strategy as a member of the executive team.

The Digital Advertising Campaign Manager will execute and optimize digital ad campaigns across various platforms, ensuring effective performance and reporting of results.

The Senior Recruiter will manage full-cycle recruiting for technical and non-technical roles, partner with leadership on talent strategy, source candidates, and maintain healthy pipelines.

The Commercial Account Executive will manage a book of business, converting leads into customers, building a pipeline, and collaborating with various teams to enhance customer acquisition and sales growth.

Partner with sales leadership to run and automate sales operations (commissions, quota tracking, deal desk, manager cadence) and deliver strategic analyses (pipeline health, capacity, segment performance) that drive recommendations and GTM decisions. Serve as cross-functional liaison and grow into target account and AE book-of-business ownership.

Own the Platform product end-to-end: prioritize and manage roadmap for infrastructure, security, AI infra, data/compliance, and internal tooling. Collaborate closely with engineers and designers to frame problems, run research, define requirements, and measure post-release impact. Operate in an async, documentation-first culture and influence stakeholders to drive technical decisions and ship complex systems.