Top Tech Jobs & Startup Jobs in Chicago, IL

Manage a portfolio of SMB and/or mid-market SaaS customers through onboarding, adoption, and growth. Drive platform education, monitor health metrics, identify upsell opportunities, and collaborate cross-functionally to surface customer feedback and improve processes.

The Lead Product Manager at Benepass will own a key product area, drive strategy and execution, and collaborate with cross-functional teams to enhance employee engagement with benefits.

The Staff Product Manager will lead fintech strategy, manage partner relationships, ensure product stability, and influence product development for Benepass, focusing on financial infrastructure.

Lead and develop a team of Customer Success Managers for SMB and Mid-Market, driving retention, renewals, product adoption, and expansion. Establish scalable processes, use data and AI/automation to optimize workflows, manage escalations, partner cross-functionally, and represent customer needs internally.

Lead the design and build of an internal, company-wide AI platform: agents, retrieval/RAG, evals, workflow runners, and CI/CD integrations. Accelerate engineering SDLC with AI-assisted coding, testing, and quality gates, then generalize platform primitives across non-engineering teams for automation, observability, and safe production use.

Build and scale QA and enablement programs for email, chat, and phone support. Create scorecards, audits, calibration, coaching, and reporting. Own Help Center, macros, voice-and-tone standards, training, and AI-driven improvements to reduce contact rate and improve team performance.