Enterprise Solutions Jobs in Chicago, IL

Salary and Benefits

At ClickUp, we believe in transparency and fairness in compensation. The range displayed reflects the minimum and maximum target salaries for the position across all US locations. Please note that the actual compensation for this position may vary and is dependent on factors such as geographic location, interview performance, years of experience, education level, and specific skills. We encourage candidates to discuss compensation expectations during the interview process to ensure alignment with their qualifications and our company’s compensation philosophy.

This position is eligible for the following benefits and perks:

• Equity

• 401k

• Health, Dental, and Vision insurance

• Spending accounts

• Life & Disability

• Paid parental leave

• Flexible paid time off

• Enhanced employee assistance program

• Employee wellness stipend

• Professional development stipend

At ClickUp, we're building the future of work: the first truly converged AI workspace unifying tasks, docs, chat, calendar, and enterprise search, all supercharged by context-driven AI. We are an AI-native company. Every team member is expected to leverage AI daily, and we evaluate AI fluency as part of our hiring process. Join us and help redefine what's possible.

This is a once-in-a-lifetime opportunity to join a hyper-growth startup focused on saving people time and making the world more productive!

ClickUp is looking for a Strategic Solutions Engineer to serve as a technical partner to our Sales and Success orgs for bringing in net new customers, expanding existing accounts, and accelerating our revenue growth. The ideal candidate is a strong strategic thinker, skilled presenter, and has enough technical aptitude to figure out solutions for any technical challenges clients experience.

Teamwork is vital to how ClickUp operates and a significant portion of your responsibilities will include working closely with Managers to understand and coordinate team needs. You should be able to work independently with little supervision, and also enjoy a fast paced and collaborative work environment. It is important that you are able to manage a range of tasks and prioritize their responsibilities, and meet deadlines with urgency and optimism.

The Role:

• Partner with sales and success to deliver technical presentations that explain our products and integrations for prospective and current clients.

• Design, develop, deploy and manage customer-specific proof of value (PoV) projects.

• Build custom reports and dynamic dashboards for prospective clients' management teams.

• Assist with the functional and technical elements of RFPs.

• Stay current on new feature releases and maintain updated demo spaces for sales.

• This role will support customers across the North East.

  
  

Qualifications:

• This is a hybrid role based in Chicago, IL with a strong preference for candidates within reasonable travel distance of Chicago. The role requires periodic in-person availability for customer onsite meetings, enterprise deal support, and team working sessions in the midwest market, including occasional co-working days with peers.

• Proven experience designing and implementing agentic workflow automation using AI platforms, including autonomous agents for task orchestration, multi-step decisioning, and cross-app integrations to deliver scalable enterprise productivity.

• 6+ years in a customer facing role with technology. Ideally pre-sales, but may also be equivalent consulting, implementation, or sales enablement experience.

• 2+ years demonstrable success working with commercial or enterprise clients

• An understanding of the application deployment processes that enable successful Cloud transformation, change management, and organizational acceptance.

• Strong customer-facing skills including the ability to influence technical and executive audiences towards the desired outcome.

• Creative problem solver with an 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 & LLMs, integration platforms (Unito, Workato, Zapier, Integromat), web services, and APIs.

• Up to 50% of travel is required for this role.

  #LI-Remote #LI-JC1

  
  

Equal Opportunity Employer

ClickUp is an Equal Opportunity Employer, and qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, or national origin.

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Visa Sponsorship

Please note we are unable to sponsor or take over sponsorship of an employment visa for roles outside of engineering and product at this time. Sponsorship for engineering and product roles is not guaranteed, but is instead based on the business needs for that specific role at that time. Please reach out to the recruiter with any questions.

Fraud Alert

ClickUp Talent Acquisition will only initiate contact via an @clickup.com email or through our official careers portal on clickup.com. We will never request fees, payments, or sensitive personal information. Please disregard any offers received outside these channels and report them to support@clickup.com.

AI Processing Notice

ClickUp may use artificial intelligence and machine learning technologies to help review and screen candidates' employment applications against role-related criteria. These tools support, but do not replace, human decision‑making. If you have questions or need an accommodation in the recruitment process, please contact us at AskPeople@ClickUp.com.