Regional Director, Commercial Sales

ClickUp • Boston, MA

21h • $250,000 - $300,000 • Hybrid

About The Position

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. 🚀

Requirements

• 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.

Nice To Haves

• 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.

Responsibilities

• 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: Associate degree