Top Tech Jobs & Startup Jobs in Chicago, IL

Manage and optimize intraday staffing and schedules for Customer Success teams. Produce forecasts, monitor phone/chat/case queues, adjust staffing in real time, drive SLA attainment, run trend analysis, develop dashboards and reports, coordinate cross-team contingency support, and communicate staffing risks and recommendations to leadership.

Lead product strategy and roadmap for a dedicated engineering team in the retirement-fintech platform. Define outcomes, measure business impact, prototype rapidly (using AI), partner across design, engineering, operations, revenue, and compliance, and use data to validate decisions and deliver scalable, compliant products.

Ensure 401(k) plan launches comply with product capabilities and regulations by auditing benefit analyses, plan documents, and system setups. Research conversion plan documents, identify and mitigate compliance risks, respond to high volumes of compliance inquiries, and collaborate with Sales Activation and onboarding teams to verify accuracy prior to plan launch.

Lead a specialized team to resolve complex, high-stakes customer incidents while building proactive quality-governance frameworks. Drive root-cause investigations, partner cross-functionally to implement engineering fixes, own post-mortems and documentation, and use data to reduce risk and improve SLA performance. Coach and scale talent, enforce accountability, and translate audit findings into training and process improvements.

Full-cycle sales role: prospect and research companies, demo the platform, manage pipeline, negotiate contracts, and close deals. Record all activities in Salesforce and use sales tech tools to meet quota.

Full-cycle Account Executive selling a fintech retirement platform to SMBs in the Mid-Atlantic: prospecting, demos, pipeline management, contract negotiation, and closing. Use Salesforce/CRMs and sales tech to track activities and exceed quota while supporting customer value and onboarding.