Top Tech Jobs & Startup Jobs in Chicago, IL

The Growth Account Executive will manage the full sales cycle, achieve sales targets, deliver demos, and collaborate cross-functionally to expand ClickUp's client base through upselling and cross-selling.

Lead and own ClickUp's technical support function: build and scale global teams, define KPIs, drive deep technical troubleshooting, partner with Product and Engineering on bug triage and incident response, and implement AI-powered workflows to improve resolution speed and quality while championing operational excellence and continuous improvement.

Lead pre-sales operations for Solutions Engineering and Consulting: drive forecasting, deal inspection, territory and capacity planning, variable compensation operations, AI/automation initiatives, executive reporting, and cross-functional alignment to accelerate deal velocity and revenue growth.

The Senior Technical Account Manager oversees customer relationships, driving engagement, onboarding, AI enablement, and business outcomes using ClickUp's platform.

The Senior Solutions Engineer will work with sales to deliver technical presentations, resolve issues, design solutions, and manage client interactions effectively.

Design, build, and operate AI-native automations and integrations across GTM systems (Salesforce, NetSuite, iPaaS). Develop LLM-powered agents, MCP integrations, and reusable automation patterns; own lifecycle, reliability, observability, and stakeholder collaboration for quote-to-cash and revenue workflows.

Lead global people operations across the full employee lifecycle, owning onboarding/offboarding, learning programs, content governance, company programs, AI agent governance, and ClickUp automations. Manage vendor relationships, ensure RTW and compliance, define lifecycle KPIs, and drive data-first continuous improvement while partnering cross-functionally and leading a team.

Lead design of collaboration workflows using AI-driven research and prototyping. Create wireframes, high-fidelity UI prototypes, and animated interactions; run usability testing and user research; automate handoffs to engineering; collaborate with PMs, engineers, and researchers to define product strategy and iterate on designs.

The Senior Product Manager at ClickUp will own the vision, roadmap, and delivery of a product area, prototype ideas using AI tools, and collaborate with cross-functional teams while leveraging data to improve outcomes.

Serve as a technical partner to Sales and Success to deliver demos, build PoVs, create reports/dashboards, respond to RFPs, design AI-driven workflow automations and integrations, and support enterprise customers with up to 50% travel and periodic onsite engagement in Chicago or Dallas markets.