Top Tech Jobs & Startup Jobs in Chicago, IL

Leads enterprise LifePRO, TPA, digital platform, and AI-enabled transformation programs from planning through deployment, stabilization, and adoption. Oversees architecture, engineering, integrations, data migration, testing, release, and production governance while aligning diverse applications to a unified strategy. Engages executive clients, manages risks and escalations, builds global delivery teams, and drives AI adoption, modernization, operational excellence, and permanent defect reduction across complex insurance ecosystems.

Lead experimentation and decision science initiatives from problem definition through recommendations. Design and analyze A/B tests, quasi-experiments, matched-market tests, and causal inference studies. Apply advanced statistics, regression, predictive modeling, machine learning, and big-data analysis using Python, R, SQL, and PySpark. Partner with stakeholders, communicate actionable findings, build reproducible workflows, and mentor analysts and junior data scientists.

Lead enterprise payer and MSO sales from prospecting through signed agreements. Sell AI value propositions to health plans and value-based care organizations, manage complex 9–18 month procurement cycles, conduct proof-of-performance deployments, and convert pilots into paid engagements. Own territory strategy, pipeline accuracy, executive relationships, and commercial feedback to product and clinical teams.

Build and maintain client-facing dashboards, embedded analytics, and reporting solutions using Power BI and related tools. Translate client needs into metrics, data models, visualizations, and insights. Validate data accuracy, support governance and privacy standards, document solutions, train users, and respond to reporting questions. Collaborate with data engineers, customer success, product, engineering, and business stakeholders while supporting AI-enabled reporting and predictive analytics for life sciences clients.

Develop qualified sales pipeline through targeted outbound prospecting, personalized multi-channel outreach, account research, consultative discovery, lead nurturing, and sales-ready handoffs. Manage complex institutional accounts, coordinate with Sales, Marketing, and Revenue Operations, maintain accurate CRM records, and use performance data to prioritize activities. Mentor colleagues, support onboarding, share best practices, and contribute to process improvements.

Provides technical customer support by triaging and resolving issues involving RelationalAI, Snowflake, Azure, databases, and graph technologies. Troubleshoots logs, stack traces, performance problems, environments, and client applications; communicates with technical and executive stakeholders; collaborates with Sales, Field Engineering, Product Management, and Product Engineering; and improves support processes, tools, products, and customer experience.

Leads a team of 7–8 Customer Success Managers serving upmarket SaaS customers. Responsibilities include coaching and developing talent, driving retention, adoption, customer value, renewals, forecasting, risk management, and operational excellence. Partners cross-functionally with Sales, Product, Support, Professional Services, Marketing, and RevOps to improve customer outcomes and scale Customer Success programs.

Owns enterprise new-logo acquisition from prospecting through contract negotiation and close. Builds pipeline, leads value-based sales cycles with senior stakeholders, delivers product demos, develops proposals and forecasts, maintains Salesforce pipeline hygiene, and partners with Marketing and Business Development. The role requires full-cycle enterprise B2B SaaS selling, quota achievement, AI-assisted sales execution, and the ability to sell workplace, facilities, HR, IT, finance, or real estate solutions.

Lead growth strategy and roadmap development for healthcare subscription products. Own the acquisition funnel from discovery through conversion, activation, and retention handoff. Define value propositions, KPIs, experimentation practices, and growth models while partnering with Analytics, Design, Research, Engineering, Marketing, and CRM teams. Use quantitative and qualitative insights to prioritize opportunities, deliver scalable subscription capabilities, and balance consumer value with business, privacy, compliance, and operational considerations.

Respond to high-volume customer inquiries by phone, live chat, and email; provide product guidance and technical support across financial offerings. Conduct outbound calls, identify customer needs, troubleshoot issues, recognize experience trends, share insights with leadership, and support teammates. The role requires strong communication, empathy, problem-solving, basic software proficiency, and ideally CRM experience.