Top Tech Jobs & Startup Jobs in Chicago, IL

Leads the development, review, quality control, and delivery of RFP responses and questionnaires. Ensures proposal accuracy, consistency, compliance, competitive positioning, and strategic alignment. Partners with Sales, Product, Operations, and subject matter experts to create customer-focused proposals that communicate Meritain Health’s capabilities and support business growth.

Leads distributed engineering teams delivering enterprise applications, APIs, integrations, cloud-native AWS solutions, microservices, and AI-enabled applications. Oversees technical direction, people management, modernization, API governance, data architecture, Agile delivery, DevSecOps, and engineering excellence. Partners with business, product, architecture, and operations stakeholders while ensuring scalable, secure, compliant solutions aligned with healthcare requirements.

Leads product vision, strategy, roadmap, backlog, requirements, and delivery for CVS Health’s Epic-integrated Documents Domain. Oversees document ingestion pipelines, downstream integrations, domain services, and document viewer UX/UI. Partners with engineering, data science, design, operations, training, and change management teams to launch and improve products. Manages Epic assessments, governance, releases, executive reporting, stakeholder alignment, user adoption, and talent development.

Leads Quality Engineering and SDET teams supporting Medicare Sales and Acquisition software. Develops AI-augmented test automation, AWS-native testing infrastructure, CI/CD quality gates, API and React testing, and agent-orchestrated SDLC workflows. Establishes governance for AI-generated test artifacts, manages engineering metrics, mentors team members, and partners with business, product, engineering, and DevOps stakeholders to improve automation coverage, quality, delivery speed, and operational efficiency.

Leads category growth strategies for CVS Media Exchange by connecting supplier objectives with CVS priorities. Develops consumer and market insights, sales narratives, commercialization opportunities, and multi-supplier campaigns. Partners across merchandising, marketing, analytics, loyalty, sales, and partner management to drive revenue and supplier investment. Leads cross-functional initiatives, business cases, innovation programs, and go-to-market planning while shaping CMX thought leadership and scalable marketing capabilities.

Lead technical strategy for a 50–150+ engineer organization, establish architecture and engineering standards, drive delivery, and partner with executives on technology investments. Embed production-grade generative AI, LLMs, agentic workflows, and ML automation into engineering. Own AI platforms, distributed systems, cloud-native backend architecture, modernization initiatives, microservices migrations, and engineering transformation while ensuring scalable, reliable outcomes.

Leads Aetna Technology account management for national and specialized clients. Builds executive relationships, supports new business sales, presents technology strategies and demonstrations, develops customer-focused content, translates technical capabilities into business value, and aligns sales, product, engineering, marketing, and account teams. Champions customer feedback, adoption, satisfaction, and consistent technology messaging across the organization.