Top Tech Jobs & Startup Jobs in Chicago, IL

Coordinates K-12 standardized testing operations, including calendars, rosters, testing sites, staffing, accommodations, devices, compliance, security, communications, and records. Supports STAAR, SAT, PSAT, and other assessments; trains staff, resolves testing barriers, maintains equipment and office supplies, enters PEIMS data in PowerSchool, and collaborates with families, schools, technology teams, vendors, and state testing authorities. The role requires two weekly San Antonio office days and up to 20% travel.

Lead a team handling complex US and UK insurance complaints, personally investigate escalated motor and property disputes, manage regulatory referrals, conduct root-cause analysis, maintain audit-ready complaint processes, and partner with Claims, Product, Engineering, QA, and Compliance to improve systems and outcomes.

Lead AI strategy and implementation across a digital agency, partnering with senior leadership and department directors. Design AI workflows and systems, run iterative sprints, manage architecture and project planning, and oversee implementation, testing, QA, adoption, and data governance. Translate AI opportunities into scalable operational plans across creative, marketing, ecommerce, lifecycle marketing, and web teams while simplifying complex concepts for cross-functional stakeholders.

The Strategic Account Executive will sell complex SaaS and network automation solutions to large enterprises, GSI/MSP organizations, and Fortune 500 companies. Responsibilities include developing territory plans, building pipeline with BDRs, engaging executive and technical stakeholders, managing long sales cycles, creating technical and commercial proposals, forecasting in Salesforce.com, leveraging sales engineers and partners, and exceeding sales quotas. The role requires enterprise technology sales experience, strong technical communication, emotional intelligence, and up to 50% travel within Tennessee.

Own the analytical strategy for a digital primary care program by defining KPIs, building dbt data models, maintaining the Snowflake/Fivetran/dbt stack, and delivering analytics, forecasting, revenue modeling, dashboards, and AI-assisted workflows. Translate patient, EHR, clinical, and operational data into actionable insights for product, care delivery, operations, leadership, health systems, and payers.

Own the full enterprise sales cycle for AI-enabled software solutions, from outbound prospecting and technical discovery through negotiation and close. Build relationships with CTOs, VP Engineering, and technical leaders; generate and manage pipeline; navigate procurement and security reviews; and collaborate with Solutions Architecture, Delivery, and Customer Success teams to support strong customer outcomes.

Leads Workday Financials implementation workstreams for public sector clients across discovery, design, configuration, testing, deployment, and post-production support. Serves as a client advisor, facilitates workshops, manages deliverables and risks, mentors consultants, reviews solution quality, and supports pre-sales, recruiting, and practice development. The role requires expertise in multiple Workday Financials functional areas and leadership across full lifecycle implementations.

Drive enterprise sales for Businessolver’s benefits SaaS platform, targeting organizations with 12,000 or more employee lives. Responsibilities include prospecting, channel partner development with brokers and advisors, platform demonstrations, consultative selling, pipeline management, presentations, opportunity tracking, reporting, and guiding deals through implementation and close. The role requires strong relationship-building and sales discovery skills, experience selling technology to large organizations, and travel up to 50%.

Own a portfolio of 30–40 mobile app clients, guiding onboarding, integration, funnel and paywall optimization, product adoption, retention, expansion, and cross-sell opportunities. Analyze subscription monetization and user acquisition performance, recommend A/B tests, resolve technical questions, gather customer feedback, and act as a strategic growth partner while driving commercial outcomes.

Leads the global Character Art discipline, overseeing artistic and technical quality, client partnerships, leadership development, organizational performance, staffing, capacity planning, and capability growth. Mentors creative leaders across India and other locations, drives solutions to quality and production issues, monitors KPIs, and supports business development. The role is remote in North America with flexible hours and periodic travel to India.