Strategic Solutions Engineer (Chicago)

ClickUp; Chicago (IL); Hybrid; USD 140,000 - 190,000; Full time

Job summary

ClickUp, a rapidly growing AI-native company, seeks a Strategic Solutions Engineer to partner with Sales and Customer Success in delivering tailored technical demonstrations and PoV projects for enterprise clients. You will design dashboards, respond to RFPs, and stay ahead of product releases while traveling up to 50% to engage customers across the Pacific Northwest and Chicago market.

The role demands strong strategic thinking, polished presentation skills, and the ability to translate complex

Qualifications

• 6+ years in a customer-facing tech role.
• 2+ years with commercial or enterprise clients.
• Experience deploying AI-powered workflows.
• Ability to travel up to 50%.
• Hybrid role based in Central U.S.

Responsibilities

• Partner with sales and success to deliver technical presentations explaining products and integrations.
• Design, develop, deploy and manage PoV projects.
• Build custom reports and dynamic dashboards for management.
• 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 Pacific Northwest

Skills

AI platforms

Pre-sales experience

Executive audience communication

Solution design

Independent / team collaboration

Strong presentation skills

Tools

Unito

Workato

Zapier

Integromat

Job description

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 Pacific Northwest

Qualifications:

• This is a hybrid role based in the Central U.S., with a strong preference for candidates within reasonable travel distance of either Chicago, IL. The role requires periodic in-person availability for customer onsite meetings, enterprise deal support, and team working sessions in the Chicago 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.
• Ability to travel up to 50% of the time

#LI-SM1 #LI-Hybrid

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.

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.

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 [e-mail].