Top Tech Jobs & Startup Jobs in Chicago, IL

The Senior GRC Analyst will manage governance, risk, compliance, and audit readiness programs, ensuring security policies and compliance frameworks are adhered to, while collaborating with various teams across the company.

Lead design and build Benepass's internal AI platform: agents, tool interfaces, retrieval, evals, workflow runners, and observability. Accelerate the engineering SDLC with AI-assisted coding, CI/CD integrations, quality automation, and testing. Ship reusable primitives and agentic workflows, enable company-wide automation, set standards and guardrails, and partner across teams to drive adoption and measurable outcomes.

Serve as primary technical contact for clients, lead implementations (API integrations, SSO, carrier migrations), troubleshoot complex data and platform issues, scope customizations, document integrations and APIs, and partner with product and engineering to translate client needs into technical requirements.

Build and scale QA and enablement programs for email, chat, and phone support. Develop scorecards, audits, calibration, coaching, Help Center content, macros, and reporting. Use data and AI to analyze quality trends, reduce contact rates, and partner cross-functionally to improve customer experience and operational KPIs.

Manage a portfolio of SMB and/or mid-market customers through onboarding to ongoing success; drive adoption, training, and product education; monitor health metrics; identify upsell opportunities; communicate customer feedback to product and engineering; develop scalable processes and collaborate cross-functionally to ensure retention and growth.

The Staff Software Engineer will design and operate financial systems involving ledgering, transaction processing, decisioning, and money movement, ensuring correctness and reliability while mentoring engineers and improving system resilience.

The role involves driving product features from research to execution, using AI tools, collaborating with design and engineering teams, and advocating for customer experience improvements.

The Senior Implementation Manager leads onboarding and implementation for high-value enterprise customers, ensuring quality experiences through effective project management and stakeholder communication.

Lead and grow an SMB/Mid-Market Customer Success team of six to drive retention, renewals, adoption, and expansion. Coach CSMs, manage escalations, establish scalable operating rhythms, implement AI and automation to improve efficiency, analyze customer and team data, build playbooks and journeys, and partner cross-functionally to deliver exceptional end-to-end customer outcomes.

Lead and develop a team of Technical Account Managers, drive operational excellence, scale TAM processes, handle complex technical escalations, and partner cross-functionally to improve product and customer outcomes. Promote AI-assisted workflows and continuous improvement while recruiting, coaching, and building repeatable playbooks for technical customer scenarios.