Top Tech Jobs & Startup Jobs in Chicago, IL

Lead end-to-end development of AI-powered features and shared AI services, own product loop from discovery to production, design data and system architecture, create reusable tooling and guardrails, mentor engineers, and ensure secure handling of sensitive school and family data.

Responsible for designing compensation models, managing headcount planning, conducting analysis for annual planning, and reporting performance metrics. Partners with cross-functional teams to streamline operations using AI tools and automation.

The GTM Compensation & Planning Analyst designs compensation plans, conducts quota-setting, maintains headcount forecasts, and collaborates with teams on financial strategies. They use AI tools to enhance productivity and ensure effective communication with executive leadership.

The Senior Analyst will design lead scoring models, automate workflows, and utilize AI tools to derive insights for sales and marketing collaboration. They will also maintain documentation to ensure team efficiency.

Lead Sales Operations for Expansion product lines, build AI-driven automated workflows and lead-scoring models, design scalable GTM processes, run funnel analytics, manage a small team, and present findings to execs.

Lead AI strategy and delivery: define technical direction, prototype and ship production AI features, build shared AI platform components (evaluation, retrieval, safety, observability), mentor senior engineers, and drive measurable business outcomes for early education customers.

Lead cross-functional delivery of AI initiatives, orchestrating technical programs across engineering, data, platform, and product. Define guardrails, evaluation frameworks, and observability for agentic systems while driving build-vs-buy tradeoffs and implementing AI-powered tooling to increase velocity and automation.

Own end-to-end AI-powered product improvements: design and build cross-cutting AI services (retrieval, evaluation, guardrails), define success metrics, prototype to production, create shared AI tooling and abstractions, shape data and system architecture for safe longitudinal signals, mentor engineers, and ship reliable, secure production systems that improve educator and family outcomes.

Lead design and delivery of AI-powered, data-driven workflows and foundations: build retrieval/evidence pipelines, durable job execution, monitoring/evaluation, data contracts, identity resolution, and reusable abstractions while partnering with product and engineering to measure adoption and impact.

The Director of Training & Enablement will manage a unified team, define an AI-first enablement strategy, and improve onboarding and performance metrics.