Enterprise Account Executive - Chicago

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.

We’re looking for an ambitious, high-energy Enterprise Account Executive based in Chicago who’s passionate about helping organizations transform the way they work. In this role, you’ll be at the forefront of driving growth by connecting with leading enterprises, understanding their unique challenges, and delivering tailored solutions that empower teams to do their best work. If you thrive in a fast-paced, collaborative environment and are excited to champion a platform that’s redefining productivity, we’d love to meet you.

The Role:

• Drive net new business by proactively identifying, engaging, and converting high-value Enterprise and Strategic prospects into customers.

• Develop and execute strategies to penetrate new accounts, build strong relationships with key decision makers, and create tailored solutions that address complex business needs.

• Consistently exceed pipeline and sales targets by generating new opportunities through outbound prospecting, networking, and leveraging marketing-qualified leads.

• Lead expansion efforts within existing Enterprise accounts by uncovering additional use cases, identifying upsell and cross-sell opportunities, and driving adoption across multiple business units.

• Deliver compelling presentations and product demonstrations to both new prospects and current customers, effectively communicating value and ROI.

• Collaborate closely with Growth, Marketing, and Customer Success teams to optimize lead generation, accelerate sales cycles, and maximize expansion revenue.

• Analyze customer segments and market trends to identify new business opportunities and continuously improve the quality of the sales pipeline, with a strong focus on both acquisition and expansion.

Qualifications:

• Minimum 3+ years experience with full-cycle ownership for large/complex deals, building consensus across key business decision makers and stakeholders, both internally and externally.

• Minimum 3+ years Enterprise SaaS sales cycle experience, including a proven track record of driving expansion sales (upsell, cross-sell, and renewals) within existing accounts.

• Proven success with a $1M+ annual quota

• Demonstrated ability to execute an expansion sales playbook and grow revenue within a defined customer base.

• Process-driven with obsessive attention to detail.

• Experience with completing and managing Requests for Information or Requests for Quotes

Desirable:

• Experience selling productivity or project management solutions, ideally in a fast-paced SaaS environment like ClickUp.

• Proven success in high-velocity, transactional sales cycles—comfortable driving quick wins while building long-term customer relationships.

• Familiarity with the land-and-expand sales model, including identifying initial entry points and rapidly expanding adoption across teams and departments.

• Ability to navigate and influence multiple stakeholders within large organizations, accelerating expansion opportunities post-initial sale.

• Exposure to customer onboarding, support, and success processes, ensuring seamless handoffs and maximizing customer value from day one.

• Passion for ClickUp’s mission to make the world more productive, and a collaborative approach to working with internal teams to deliver exceptional customer experiences.

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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If you are a Philippine Job Applicant, please also see our Philippine Data Privacy Notice for further details.

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 View email address on click.appcast.io.

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 View email address on click.appcast.io.