Top Tech Jobs & Startup Jobs in Chicago, IL

Build and maintain Pit Viper, a reusable design system and component library, primarily with Vue and Web Components. Partner with designers and engineers to implement polished, accessible, responsive product experiences directly in application code. Define component APIs, interactions, states, documentation, testing, and release practices while improving consistency across Vue and server-rendered surfaces. Review and resolve usability, visual, behavioral, and accessibility issues, and help product teams ship higher-quality experiences more efficiently.

Create brand and marketing assets including presentations, sales collateral, social and display graphics, email, web pages, and event materials. Apply and extend established brand guidelines and component libraries while collaborating with marketing, product, design, and sales teams. Manage feedback, shifting priorities, and multiple requests in a fast-paced environment. Motion design, Webflow, and Canva experience are advantageous.

Build full-stack Django applications with a frontend focus, creating intuitive, interactive, and performant data visualizations for complex healthcare pricing data. Collaborate with product and engineering teams to define user experiences, prioritize features, write scalable code, test and debug systems, improve existing functionality, and translate user requirements into technical solutions.

Build and lead the sales enablement function, owning new-hire ramp, ongoing rep coaching, performance analysis, sales training, product launch enablement, and sales content. Partner with Sales leadership, Revenue Operations, and Product Marketing to improve rep effectiveness across complex, multi-stakeholder enterprise deals and evolving product lines.

Leads corporate strategy and operational priorities for the Employer function. Partners with executives, conducts market and competitive analysis, identifies growth opportunities, develops strategic frameworks, and drives cross-functional initiatives. Acts as a senior leadership advisor, coordinates stakeholders and resources, prepares executive communications, and supports external relationships, industry events, partnerships, and strategic messaging.

Build and operate the platform: manage EKS/Kubernetes, implement GitOps (ArgoCD), maintain CI/CD (GitHub Actions), define SLIs/SLOs, lead incident response/on-call and post-mortems, design observability (Datadog, Sentry, CloudWatch, Grafana), automate infra with IaC (Terraform/CloudFormation/Crossplane), write Python tooling, and shape platform architecture and self-service workflows.

Lead performance investigations across the data product stack to diagnose and fix slow queries and UX issues. Design data architecture changes, build benchmarks, measure latency/throughput/cost (ClickHouse Cloud), prototype solutions, instrument monitoring, and partner with product and engineering to balance responsiveness, scalability, and cost.

Lead enterprise sales into the Employer segment: own full sales cycle, build executive relationships, negotiate contracts, manage pipeline and forecasts, collaborate with Product, update Salesforce, and solve client business challenges to drive revenue.

Responsible for sales and expansion at Turquoise Health, managing the full sales cycle with high-level executive stakeholders in healthcare.

Lead the Contracts product roadmap for a B2B healthcare SaaS platform, applying deep reimbursement and managed care expertise. Partner with AI engineers to build contract-understanding models, drive adoption, iterate on workflows, create business cases, and coordinate cross-functionally with Legal, Finance, Sales, and SMEs to ensure compliant, revenue-aligned contract execution.