Top Tech Jobs & Startup Jobs in Chicago, IL

Manage a portfolio of California large-group employer clients (100–2,000 lives), lead renewals, open enrollment, compliance, vendor deployment, and member education. Design benefit strategies, create presentations and financial reporting, strengthen client relationships, and collaborate with internal teams to improve service delivery.

The Enterprise Account Executive will drive sales growth by identifying, developing, and closing new business opportunities. The role requires experience in technical sales of software solutions, particularly AI technologies, along with strong communication, negotiation skills, and a network of decision-makers.

The Project Manager will manage the implementation of enterprise SaaS solutions in the utility industry, ensuring project success and customer satisfaction.

Lead design of AI-supported member and care experiences, defining interaction models, prototyping AI-driven flows, and designing service blueprints. Partner with product, engineering, data, clinical, and research teams to translate AI capabilities into trustworthy, clinically appropriate, and scalable experiences. Create prototypes, design artifacts, evaluation loops, and influence senior stakeholders to align user needs, business goals, and technical constraints.

Lead Omada's investor relations and capital markets strategy as a public company: craft and communicate the equity story, engage investors and analysts, manage earnings and disclosure processes, analyze investor models and ownership trends, and partner with Finance, Legal, and executives on guidance, investor targeting, and capital-markets activities.

Part-time Director-level HR Business Partner supporting Commercial, Corporate Strategy & Ops, and Finance. Leads organizational design, workforce and capability planning, change leadership, and leadership coaching. Uses AI fluency and people data to inform strategy, redesign roles for human-AI collaboration, streamline HRBP workflows, and measure P&C impact. Partners with centers of excellence and employee relations; advises on complex people issues. Requires travel up to ~25-30% and work during core PST business hours.

Manage end-to-end analytics for performance guarantees across strategic accounts: execute recovery and accrual analytics, build SQL-based pipelines and Looker dashboards, support RFPs/renewals with scenario modeling, partner with Sales/Customer Success and Data Engineering, and present technical findings to internal leaders and clients to mitigate financial risk and drive actionable insights.

As a Customer Support Representative, you will assist customers with health insurance queries across multiple channels, resolve issues, and advocate for product improvements while maintaining high productivity and empathy.

Lead state and federal government affairs for hemp beverage policy. Shape regulations, run advocacy campaigns, build regulator and industry relationships, advise leadership on market entry and compliance, and partner with product, legal, and commercial teams to enable growth across states.

Lead partner-focused go-to-market programs to drive pipeline, revenue, and adoption through AWS, WWT, and strategic partners. Create partner-ready positioning, enablement, competitive intelligence, and co-marketing campaigns. Build scalable enablement and partner portal content, align cross-functionally with Product, Sales, and Marketing, and serve as product marketing owner for strategic partnerships.

Own FP&A deliverables including budgeting, forecasting, variance analysis, and rolling forecasts. Build driver-based financial models, consolidate inputs, support quarterly and annual planning, automate workflows, and contribute to executive and investor reporting.

Operate and optimize Keeper's cloud databases across dev, QA and production. Manage MySQL on AWS (RDS), ensure high availability, performance tuning, backups, replication, disaster recovery, schema change control with IaC tools, monitoring, incident response, automation, and participate in 24/7 on-call rotation while collaborating with engineering and DevOps teams.

The Engineering Manager will lead the Web & Add-ins team, driving product development and team optimization while ensuring project success and best practices.