Strategic Solutions Engineer, Enterprise (Chicago)

About this role

Partner with Sales and Customer Success to support enterprise prospects and customers through technical presentations, tailored proof-of-value projects, and solution design. The role also supports account expansion and revenue growth, with a focus on customers across the Northeast.

About the company

ClickUp is a work management platform that combines tasks, docs, goals, and collaboration tools for teams running projects across functions.

The team

Customer Experience; Solutions & Enablement

Stack

What you'll do

• Deliver technical presentations on ClickUp products and integrations.
• Design, develop, deploy, and manage customer-specific proof-of-value projects.
• Build custom reports and dynamic dashboards for prospective clients.
• Support functional and technical elements of RFPs.
• Maintain current sales demo environments and stay up to date on product releases.

What we're looking for

• 6+ years of customer-facing experience in technology, ideally in pre-sales or equivalent consulting, implementation, or sales enablement.
• At least 2 years of demonstrated success with commercial or enterprise clients.
• Experience designing and implementing AI agentic workflow automation, including task orchestration, multi-step decision-making, and cross-app integrations.
• Hands-on experience with AI and LLMs, integration platforms, web services, and APIs.
• Strong presentation and influencing skills with technical and executive audiences.
• Experience with business process mapping, diagramming, consumption-based selling, and value selling.
• Understanding of cloud transformation, change management, and organizational adoption.
• Able to work onsite in Chicago three days per week and travel up to 50%.

Benefits

• Equity
• 401(k)
• Health, dental, and vision insurance
• Paid parental leave
• Flexible paid time off
• Wellness stipend
• Professional development stipend