Top Tech Jobs & Startup Jobs in Chicago, IL

Lead a team of ML engineers to design, build, and productionize LLM/GenAI and agentic systems (retrieval, tool use, orchestration). Collaborate cross-functionally with MLOps, product, and data science, review code, mentor engineers, run technical evaluations and proofs-of-concept, and ensure reliable, safe ML deployments for a large SaaS product.

Administer and govern the revenue enablement tech stack (LetterAI, Seismic, Gong, Consensus), configure certification and AI role-play workflows, manage content taxonomy and access, build adoption and certification reports, deliver end-user training, and partner with Operations and Programs to align tools to launches and OKRs.

Lead the Customer Success Enablement function to develop onboarding, adoption, expansion, and retention programs. Build and coach a high-performing enablement team, align cross-functional launch priorities, measure OKR-tied outcomes, run Gong call reviews, and create AI-assisted content and role-play certification to drive expansion ARR and retention.

Lead Field Sales Enablement to translate business priorities into measurable seller and manager behaviors that improve pipeline, productivity, and revenue. Build and coach a team of enablement partners, partner with Sales leaders to set OKRs and KPIs, run Gong review rhythms, develop AI-assisted content and certifications, tailor multi-product enablement by segment, and own onboarding and operating rhythms with cross-functional partners.