Strategic Solutions Engineer (AI)

Location: Hybrid role based in Chicago, IL, with periodic in-person availability for customer onsite meetings, enterprise deal support, and team working sessions in the Midwest market. Up to 50% travel is required. The role supports customers across the Northeast.

Salary: $175,000–$225,000 annually, plus equity. Actual compensation varies by location, interview performance, experience, education, and skills.

Company

ClickUp is a hyper-growth startup building an AI-native workspace that unifies tasks, docs, chat, calendar, and enterprise search.

What you will do

• Partner with Sales and Success to deliver technical presentations explaining ClickUp products and integrations to prospective and current clients.
• Design, develop, deploy, and manage customer-specific proof-of-value projects.
• Build custom reports and dynamic dashboards for prospective clients’ management teams.
• Assist with the functional and technical elements of RFPs.
• Maintain current product knowledge and updated demo spaces for Sales.
• Coordinate team needs with Managers while independently prioritizing tasks and meeting deadlines.

Requirements

• Proven experience designing and implementing agentic workflow automation using AI platforms, including autonomous agents for task orchestration, multi-step decisioning, and cross-app integrations.
• 6+ years of experience in customer-facing technology roles, ideally in pre-sales or in equivalent consulting, implementation, or sales enablement work.
• 2+ years of demonstrable success working with commercial or enterprise clients.
• Understanding of application deployment processes supporting cloud transformation, change management, and organizational acceptance.
• Strong customer-facing communication skills, including the ability to influence technical and executive audiences toward desired outcomes.
• Creative problem-solving ability, eagerness to learn new technologies, and sufficient technical background to support lightweight custom solutions.
• Experience with business process mapping and diagramming, consumption-based selling, and value selling to drive customer outcomes and align solutions with business objectives.
• Hands-on experience with AI and LLMs, integration platforms including Unito, Workato, Zapier, and Integromat, web services, and APIs.
• Ability to travel up to 50% and attend periodic in-person customer and team sessions in the Midwest.

Culture & Benefits

• AI-native work environment where employees are expected to leverage AI daily and demonstrate AI fluency during hiring.
• Equity, 401(k), health, dental, and vision insurance, spending accounts, and life and disability coverage.
• Paid parental leave, flexible paid time off, and an enhanced employee assistance program.
• Employee wellness and professional development stipends.
• Collaborative, fast-paced environment with opportunities to work independently and with cross-functional teams.

Hiring process

• AI fluency is evaluated as part of the hiring process.
• ClickUp does not provide or take over employment visa sponsorship for roles outside Engineering and Product.