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ClickUpClickUpBoston, MA

Regional Director, Commercial Sales

Lead and coach a team of Account Executives in the commercial/SMB segment across AMER. Drive revenue targets, pipeline, hiring, and scalable sales processes in a high-growth AI workspace company. Requires significant B2B SaaS sales leadership experience.

250k – 275k/yr
Hybrid7+ YOESales Engineering

About the role

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.

Skills

B2B SaaS Salessales team leadershipPipeline ManagementForecastingCRMMEDDICOutbound Sales
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