Top Tech Jobs & Startup Jobs in Chicago, IL

Lead growth and lifecycle marketing by translating complex AI product capabilities into compelling copy and multi-touch programs. Build AI-powered marketing systems, run high-velocity experiments across funnel channels, own lifecycle and in-app messaging, and partner with product and growth teams to drive onboarding, retention, expansion, and feature launches.

Partner with PLGTM leaders to advise on performance, development, and employee relations; support performance cycles, talent reviews, and case management; enable managers through coaching and tools; drive people operations excellence; and lead AI-first transformation by building AI agents and automations to reduce repetitive work.

The Senior AI Engineer will develop AI-powered features, mentor engineers, and integrate large language models to enhance user experiences and ensure product reliability.

Develop AI-powered features, collaborate with teams, integrate LLMs, ensure production quality, mentor engineers, and stay updated on AI trends.

Lead strategy and execution for Technical Account Management (TAM) operations across Services and Customer Success. Own systems, automation, planning, forecasting, quality, and insights; design and operate AI-driven workflows and agentic automation; drive capacity planning, renewals forecasting, and service quality; influence cross-functional stakeholders and scale operational capabilities to improve retention, revenue, and CX outcomes.

Lead ClickUp's organic acquisition strategy across Google, LLMs, and emerging discovery surfaces. Build AI-powered workflows and agents, oversee technical SEO and content portfolio, partner cross-functionally, define measurement frameworks, and own the SEO roadmap and external partnerships to maximize AI and search visibility.

Partner with GTM leaders to turn large datasets into actionable insight, build dashboards and forecasting models, analyze pipeline/retention/productivity, and implement automation and AI-enabled workflows to improve revenue performance and GTM operations.

Design, build, and maintain AI-driven automations and integrations across Zendesk, Salesforce, ClickUp, and chatbots to reduce manual support work, improve CX, and measure automation impact. Own end-to-end lifecycle, monitor reliability, iterate with stakeholders, and expand LLM capabilities and reusable AI patterns.

Lead Cloud Platform to build scalable, secure, and cost-efficient AWS infrastructure (EKS-focused), align stakeholders, automate shard buildout, reduce incidents via hardened ingress and Terraform guardrails, manage distributed senior teams and AWS spend, and deliver a cloud roadmap tied to AI and enterprise goals.

Lead and develop a Technical Account Management team for mid-market and enterprise AMER accounts to drive onboarding, adoption, retention, and expansion. Build operating rhythms, use health and adoption data to prioritize interventions, run renewal and executive reviews, partner cross-functionally, and operationalize AI-driven workflows and playbooks to scale coverage and improve outcomes.