Top Tech Jobs & Startup Jobs in Chicago, IL

Build and evolve machine learning tooling and infrastructure for AI-powered clinical solutions, including automated prompt tuning, feedback loops, model benchmarking, experimentation, and evaluation. Partner with data science, clinical, software engineering, and product teams to develop scalable solutions, solve ambiguous technical problems, establish engineering standards, and provide technical mentorship without direct management responsibility.

Leads governance, coordination, reporting, and execution for Marketplace Network Strategy programs focused on affordability, provider reimbursement, and enterprise network strategy. Establishes goals, controls, metrics, budgets, documentation, and change-management practices; partners with executives and cross-functional healthcare teams; manages risks, requirements, testing, training, stakeholder adoption, and continuous improvement across complex initiatives.

Lead technical discovery and solution architecture for enterprise payment customers and prospects. Design secure, scalable integrations involving tokenization, payment flows, processors, APIs, and credential portability. Support opportunities through demos, proofs of concept, RFPs, security reviews, architecture approval, and implementation handoff. Partner with Sales, Account Management, Product, Engineering, and customers to manage technical risks, influence the product roadmap, and develop reusable architectures and enablement materials.

Lead the strategy, roadmap, and transformation of eHealth’s consumer health insurance marketplace and online enrollment experience. Drive AI-native shopping tools, audience segmentation, growth funnels, UX optimization, and enterprise website governance. Partner with engineering, data science, marketing, legal, compliance, and business teams to improve conversion, customer trust, and long-term value. Mentor product leaders, guide executives, prioritize backlogs, oversee Agile delivery, and use analytics and experimentation to measure outcomes.

The Controller leads accounting operations, financial reporting, month-end and year-end close, internal controls, cash management, audit coordination, tax processes, and complex SaaS revenue accounting. The role oversees quote-to-cash controls and integrations across Salesforce, Certinia, Avalara, and Qobra, including ASC 606 revenue recognition, usage-based billing, deferred revenue, commissions, and sales tax. This leader will manage the accounting team and improve systems, processes, documentation, and cross-functional financial operations.

Build and lead Leena AI’s enablement function across internal teams, customers, and partners. Develop AI-first knowledge systems, in-product guidance, documentation, communities, playbooks, and partner accreditation. Establish enablement strategy, hire and manage the team, collaborate cross-functionally, and measure outcomes including self-service adoption, answer deflection, time to value, community engagement, and partner-led go-lives.

Leads engineering and manufacturing projects from requirements through delivery, managing scope, schedules, budgets, resources, risks, change control, vendors, KPIs, and stakeholder communications. Coordinates cross-functional teams, drives issue resolution, supports training and continuous improvement, and ensures projects meet quality, cost, and timeline objectives.

Serve as a technical advisor supporting account managers through fraud and compliance upsell and cross-sell opportunities. Deliver customized product demonstrations, complete security reviews, develop solution designs, and translate customer needs into platform improvements. The role requires strong technical communication, API and coding knowledge, fraud or compliance experience, and the ability to work with financial institutions and global enterprises in a remote environment.

The AI Business Analyst leads discovery, process mapping, use-case prioritization, and requirements definition for AI, analytics, reporting, and automation projects. They translate business needs into user stories and acceptance criteria, maintain traceability, assess data readiness and impacts, support backlog refinement and user acceptance testing, document validation results, and prepare process guidance and handover materials. The role connects client stakeholders with technical delivery teams while tracking risks, dependencies, decisions, and business outcomes.

Serves as PharmaLogic’s senior legal advisor and strategic partner, overseeing commercial contracts, intellectual property, litigation, regulatory compliance, corporate governance, transactions, employment matters, enterprise risk, and outside counsel. The General Counsel manages the legal function, develops policies and contracting processes, supports regulated pharmaceutical and manufacturing operations, and provides practical guidance that enables growth while mitigating legal and regulatory risks.