Top Tech Jobs & Startup Jobs in Chicago, IL

Lead financial modelling and analytics for pricing, monetization, and strategic finance. Build scenario and profitability models, apply AI/ML (LLMs, predictive models) to accelerate modelling and reporting, deliver executive-ready profitability reporting, and partner with FP&A, Sales Ops, and GTM leaders to support strategic decisions.

Lead cross-functional customer operations launches for SaaS healthcare solutions from pilot to commercial availability. Create and manage launch plans, define operational metrics, prioritize resources and budgets, drive improvements, provide risk/issue reporting, and coach teams to ensure customer time-to-value and company time-to-revenue.

Lead multiple Agile development teams to deliver enterprise software; own architecture and technical design; drive end-to-end delivery, mentor engineers, champion AI-first innovation, ensure release quality, partner with product, and improve operational excellence.

The Principal AI Platform Engineer will design and maintain the infrastructure for AI systems, ensuring integration, security, and scalability for GenAI products.

As a Principal Software Data Engineer, you'll lead the design, development, and optimization of large-scale data platforms and pipelines, ensuring data governance and driving innovation in a collaborative environment.

The Senior Software Engineer will develop and maintain big data applications, focusing on distributed computing, automation, and collaboration with teams to enhance healthcare solutions.

Lead strategy and execution of customer engagement and advocacy programs across online communities, user groups, nurture campaigns and integrations. Drive community growth, moderation governance, stakeholder alignment, cross-functional campaign activation, data-driven insights to improve adoption, reduce churn, and demonstrate business value.

Lead and coordinate high-visibility customer escalations across engineering, product, customer success, and support. Build the escalation management function, create data-driven recovery plans, use metrics to improve processes, and communicate outcomes to technical and executive stakeholders.

Lead and scale UX, content design, and user research across a complex B2B healthcare product portfolio. Define experience strategy, governance, design system adoption, AI-enabled interactions, and measurable UX quality metrics. Partner with Product and Engineering, reduce ambiguity, embed UX early in discovery, and build high-performing design teams to improve usability, adoption, accessibility, and customer satisfaction.

Seeking dynamic sales professionals in healthcare, SaaS, or enterprise software to join PointClickCare and make a difference through innovative technology.