Strategic Solutions Engineer (AI)

Location: United States; hybrid role based in the Central U.S. with a strong preference for candidates within reasonable travel distance of Chicago, Illinois. Periodic in-person availability is required for customer meetings, enterprise deal support, and team working sessions. Travel may be required up to 50% of the time.

Salary: Estimated annual OTE of $175,000–$225,000, plus equity.

Company

ClickUp is an AI-native productivity software company building a unified workspace for tasks, documents, chat, calendar, and enterprise search.

What you will do

• Partner with Sales and Customer Success to deliver technical presentations covering products and integrations.
• Design, develop, deploy, and manage customer-specific proof-of-value projects.
• Build custom reports and dynamic dashboards for prospective clients' management teams.
• Support the functional and technical components of RFP responses.
• Maintain current product knowledge and updated demo environments for Sales.
• Coordinate with managers and support customers across the Pacific Northwest.

Requirements

• 6+ years of experience in a customer-facing technology role, preferably in pre-sales, consulting, implementation, or sales enablement.
• At least 2 years of demonstrated success working with commercial or enterprise clients.
• Experience designing and implementing agentic workflow automation with autonomous agents, multi-step decision-making, and cross-application integrations.
• Hands-on experience with AI, LLMs, integration platforms such as Unito, Workato, Zapier, and Integromat, web services, and APIs.
• Understanding of cloud deployment processes, change management, organizational adoption, business process mapping, consumption-based selling, and value selling.
• Strong customer-facing communication, presentation, prioritization, problem-solving, and technical solution design skills.

Nice to have

• Previous pre-sales experience.
• Experience creating lightweight custom technical solutions.
• Experience influencing technical and executive audiences.

Culture & Benefits

• Fast-paced, collaborative environment with autonomy and close coordination with managers.
• Equity opportunity.
• 401(k), health, dental, and vision insurance.
• Spending accounts, life and disability coverage, paid parental leave, and flexible paid time off.
• Employee wellness, professional development, and enhanced employee assistance stipends.
• AI fluency is evaluated during the hiring process, and employees are expected to use AI daily.

Hiring process

• AI fluency is assessed as part of the hiring process.
• Employment visa sponsorship is not available for this non-engineering and non-product role.