Strategic Solutions Engineer, Enterprise (Chicago)

ClickUp•Chicago, IL
•$175,000 - $225,000•Hybrid

About The Position

ClickUp is seeking a Strategic Solutions Engineer to act as a technical partner to its Sales and Success organizations. The role supports acquiring new customers, expanding existing accounts, and accelerating revenue growth. The successful candidate will be a strategic thinker and skilled presenter with the technical aptitude to address customer challenges. The role involves close coordination with managers, independent work with little supervision, and collaboration in a fast-paced environment while managing priorities and deadlines. This is a hybrid role based in Chicago, Illinois, supporting customers across the Northeast. The company strongly prefers candidates within reasonable travel distance of Chicago. Periodic in-person availability is required for customer onsite meetings, enterprise deal support, and team working sessions in the Midwest market, including occasional coworking days with peers. Travel of up to 50% is required.

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 for enterprise productivity.
  • At least 6 years in a customer-facing technology role; pre-sales experience is preferred, though equivalent consulting, implementation, or sales enablement experience may qualify.
  • At least 2 years of demonstrated success working with commercial or enterprise clients.
  • Understanding of application deployment processes that support cloud transformation, change management, and organizational acceptance.
  • Strong customer-facing skills, including the ability to influence technical and executive audiences toward desired outcomes.
  • Creative problem-solving skills, eagerness to learn new technologies, and sufficient technical background to assist with lightweight custom solutions.
  • Demonstrated ability in business process mapping and diagramming, with experience in 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 (Unito, Workato, Zapier, or Integromat), web services, and APIs.
  • Availability for up to 50% travel.
  • Ability to work independently with little supervision and collaborate in a fast-paced environment while prioritizing tasks and meeting deadlines.

Nice To Haves

  • Pre-sales experience.
  • Reasonable travel distance from Chicago.

Responsibilities

  • 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 requests for proposals (RFPs).
  • Stay current on feature releases and maintain updated sales demo spaces.
  • Coordinate with managers to understand and address team needs.
© 2026 Teal Labs, Inc
Privacy PolicyTerms of Service