Top Tech Jobs & Startup Jobs in Chicago, IL

Serve as a legal-domain pre-sales consultant for mid-market law firms: lead discovery, deliver tailored Clio product demos and pilots, advise on safe AI adoption, convert practice needs into workflows, influence product via user insights, mentor sales and success teams, and represent Clio in legal tech thought leadership.

Leads and develops a technical VoIP support and implementation team while personally handling complex SIP troubleshooting and escalations. Owns team scheduling, capacity, performance, SLAs, documentation, provisioning standards, call-flow configuration, number porting, messaging compliance, and onboarding quality. Partners with Engineering, Product, and Customer Success leadership on communications initiatives, monitors service metrics, hires team members, and contributes to cross-functional VoIP projects.

Design, develop, and maintain secure integrations across NetSuite, Coupa, Leapfin, and other enterprise systems. Build iPaaS workflows, custom connectors, webhook and event-driven automations, bulk synchronization processes, monitoring, error handling, and retry mechanisms. Translate finance requirements into technical specifications and data mappings, support implementation projects, document architectures, and maintain audit readiness. Apply AI-powered tooling to automate finance operations while ensuring compliance, security, and reliable handling of sensitive financial data.

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.

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.