ClickUp
Strategic Solutions Engineer (Chicago)
About this role
ClickUp seeks a Strategic Solutions Engineer to bridge technical and sales functions, delivering product demonstrations, designing proof-of-concept projects, and solving customer challenges for new and expanding accounts. The role combines technical problem-solving with strategic customer engagement, requiring AI and integration platform expertise in a hybrid Chicago or Dallas position.
What you'll do
- Deliver technical product presentations and integration demos to prospects and clients alongside sales and success teams
- Design and implement customer-specific proof of value projects with custom reporting and dashboards
- Support RFP responses by addressing functional and technical requirements
- Maintain updated demo environments and stay current with feature releases
- Assist with enterprise deal support and customer onsite meetings
- Map business processes and recommend AI-driven workflow automation solutions
What they're looking for
- AI and LLM platforms (agentic workflows, autonomous agents)
- Integration platforms (Unito, Workato, Zapier, Integromat)
- APIs and web services
- Business process mapping and diagramming
- Technical presentation and executive communication
- Cloud transformation and change management
- Proof of concept design and implementation
- Value selling and consumption-based selling methodologies
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ClickUp
ClickUp builds a work management and productivity platform while investing in AI-powered automation and integration capabilities across its go-to-market and business systems infrastructure. The company is hiring for DevOps engineers, solutions engineers, and business systems engineers to support cloud infrastructure, customer implementations, and intelligent workflow automation.
- Website
- clickup.com
Likely interview questions
- Can you walk us through a technical proof of value project you've designed for a prospective client? What was the outcome and how did it influence the deal?
- Describe your hands-on experience with AI, LLMs, and integration platforms like Zapier, Workato, or similar tools. What agentic workflows have you built or implemented?