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Strategic Solutions Engineer, Enterprise (Chicago)

ClickUp - Chicago, IL, United States - Hybrid - posted 2026-10-22

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ClickUp is seeking a Strategic Solutions Engineer to serve as a technical partner bridging Sales and Success organizations. You will drive net new customer acquisition, expand existing accounts, and accelerate revenue growth by combining strategic thinking, strong presentation skills, and technical problem-solving capabilities. Key responsibilities include: - Partner with sales and success teams to deliver technical presentations explaining ClickUp's products, integrations, and AI capabilities to prospective and current enterprise clients - Design, develop, deploy, and manage customer-specific proof of value (PoV) projects that demonstrate business impact - Build custom reports and dynamic dashboards for prospective clients' management teams - Support functional and technical elements of RFPs (Request for Proposals) - Stay current on new feature releases and maintain updated demo environments for the sales team - Support customers across the North East region with periodic travel to customer sites This is a hybrid role based in Chicago with a strong preference for candidates within reasonable travel distance. The position requires periodic in-person availability for customer onsite meetings, enterprise deal support, and team collaboration in the Midwest market, including occasional co-working sessions with peers. Up to 50% travel is required. ClickUp is an AI-native company building a converged workspace unifying tasks, docs, chat, calendar, and enterprise search powered by context-driven AI. You'll work in a fast-paced, collaborative environment supporting a hyper-growth startup focused on productivity and time-saving solutions. REQUIREMENTS: - 6+ years in a customer-facing role with technology (pre-sales, consulting, implementation, or sales enablement experience preferred) - 2+ years demonstrable success working with commercial or enterprise clients - Proven experience designing and implementing agentic workflow automation using AI platforms, including autonomous agents for task orchestration, multi-step decisioning, and cross-app integrations - Understanding of application deployment processes enabling Cloud transformation, change management, and organizational acceptance - Strong customer-facing skills with ability to influence technical and executive audiences - Creative problem solver with eagerness to learn new technologies and sufficient technical background for lightweight custom solutions - Demonstrated ability in business process mapping and diagramming - Experience with consumption-based selling and value selling methodologies - Hands-on experience with AI & LLMs, integration platforms (Unito, Workato, Zapier, Integromat), web services, and APIs - Willingness to travel up to 50% for customer engagement and support

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