Regional Director, Commercial Sales

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. 🚀

What You’ll Own

• Lead, coach, and develop a team of Account Executives focused on the commercial segment across AMER.

• Drive pipeline generation, deal execution, and consistent attainment of regional revenue targets.

• Build a strong operating cadence around forecasting, pipeline inspection, deal reviews, rep development, and performance management.

• Hire, ramp, and retain high-performing talent while creating an ambitious, inclusive, and motivating team culture.

• Improve sales process scalability through better use of CRM data, performance metrics, and repeatable best practices.

• Partner closely with Growth, Marketing, Operations, and Product to improve conversion, support important accounts, and remove friction in the customer journey.

• Reinforce high standards for thoughtful, value-based selling and customer-first leadership.

• Report on performance, pipeline health, forecast accuracy, and improvement opportunities to senior leadership.

Required Qualifications

• Significant experience leading B2B SaaS sales teams in a commercial, SMB, or mid-market motion.

• Strong understanding of selling across AMER markets and how regional nuance shapes coaching, hiring, and execution.

• Proven track record coaching high-performing sellers and improving team productivity, forecast quality, and revenue outcomes.

• Experience building or scaling repeatable new-business and outbound motions.

• Strong analytical and operational instincts, with comfort using CRM data, sales metrics, and pipeline insights to drive decisions.

• Excellent communication, collaboration, and change-management skills.

• Ability to influence partners across Marketing, Product, Operations, and other go-to-market functions.

Preferred Qualifications

• Experience in a high-growth B2B SaaS environment.

• Familiarity with structured sales methodologies such as MEDDIC.

• Experience leading distributed teams across multiple U.S. regions or broader AMER time zones.

• Experience improving rep ramp, inspection cadence, and frontline manager effectiveness at scale.

• Bachelor’s degree or equivalent practical experience.

Location & Travel

• This role is approved for the United States and is expected to be based in Boston.

• Candidates should be comfortable working in a hybrid environment and coming into the office 2–3 days per week.

• Travel may be expected for team connection, customer meetings, and key planning moments as needed.

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.

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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 [email protected].