Regional Director, Commercial Sales

About the role

ClickUp is actively searching for a Regional Director to take ownership of the Commercial Sales function and lead the team responsible for driving revenue across the Americas. This position requires a strategic leader who will guide a team of Account Executives, ensuring they operate with precision and a shared vision for success. The role focuses on establishing a sustainable and high-performing sales culture that thrives within a hybrid work model. You will be responsible for setting the tone and standards for commercial selling excellence throughout the region. The ideal candidate will balance operational rigor with the ability to inspire and develop talent. Success in this role means fostering collaboration between internal stakeholders to create a unified go-to-market strategy. You will be a key driver in aligning commercial activities with the broader business objectives of ClickUp. This is an opportunity to shape the future of sales for a leading productivity platform.

Key facts

What you'll do

• Direct and mentor a team of Account Executives within the commercial segment across the AMER region, providing strategic direction and hands-on coaching.
• Generate a robust sales pipeline, execute complex deals, and consistently achieve or exceed predefined regional revenue goals and quotas.
• Establish and maintain a consistent operational rhythm for forecasting accuracy, pipeline analysis, deal reviews, and comprehensive performance management.
• Recruit high-caliber talent, oversee structured onboarding programs, and retain top performers while cultivating an ambitious, collaborative, and inclusive team culture.
• Enhance sales process efficiency by leveraging CRM data, analyzing performance metrics, and implementing repeatable best practices across the team.
• Collaborate closely with teams in Growth, Marketing, Operations, and Product to identify synergies that improve conversion rates and elevate the overall customer experience.
• Uphold the highest standards for value-based selling, ensuring that the team articulates ROI and positions solutions effectively to key stakeholders.
• Provide detailed reports on team performance, pipeline health, forecast accuracy, and specific improvement areas to senior leadership for strategic review.
• Own the development and execution of sales playbooks tailored to the commercial segment to ensure consistency and scalability.
• Drive the adoption of data-driven decision-making to optimize territory coverage and prioritize high-value opportunities for the team.
• Partner with Customer Success to ensure seamless transitions and alignment on account expansion and retention strategies.
• Identify and mitigate risks within the sales cycle, proactively addressing blockers that could hinder deal progression or team performance.
• Champion the adoption of new sales technologies and methodologies to maintain a competitive edge in the marketplace.
• Lead by example in demonstrating resilience, adaptability, and a relentless focus on achieving ambitious targets in a fast-paced environment.

Requirements

• Possess significant experience leading B2B SaaS sales teams specifically within commercial, SMB, or mid-market segments in the Americas.
• Demonstrate a strong understanding of selling dynamics in AMER markets, including the regional nuances required for effective coaching and execution.
• Show a proven track record of coaching high-performing sellers and implementing strategies that measurably improve team productivity and revenue generation.
• Have direct experience building or expanding new-business generation and outbound sales motions that yield predictable results.
• Exhibit strong analytical and operational skills, utilizing CRM data and sales performance metrics to inform strategy and guide decisions.
• Communicate with exceptional clarity and foster strong collaboration with cross-functional partners across Marketing, Product, and Operations.
• Display a capacity to influence stakeholders and drive change-management initiatives without direct authority over partner teams.
• Adhere to the requirement of having a Bachelor's degree or equivalent practical experience that demonstrates a foundational knowledge of business principles.
• Be authorized to work in the United States and not require work authorization sponsorship from the company for this position.
• Commit to a hybrid work arrangement, requiring physical presence in the Boston office for 2 to 3 days per week as scheduled.
• Possess the legal right to travel domestically within the United States for business purposes, including attendance at team events and client meetings.
• Be willing to undergo periodic background checks as required by company policy for employment in a commercial sales role.

Nice to have

• Have hands-on experience within a high-growth B2B SaaS environment where agility and rapid scaling are common.
• Be familiar with structured sales methodologies such as MEDDIC, champion, and advocate for their application.
• Have a track record of managing distributed sales teams across multiple US regions or diverse AMER time zones effectively.
• Demonstrate success in improving key rep ramp-up times, inspection cadence adherence, and frontline manager effectiveness at scale.
• Hold a Bachelor's degree or equivalent practical experience that contributes to a well-rounded professional background.

Practical notes

• This role does not have visa sponsorship available; candidates must be authorized to work in the United States.
• The engagement is classified as full-time, requiring a commitment to the hybrid schedule.
• Travel may be necessary to attend team events, conduct customer meetings, and participate in strategic planning sessions.
• It is important to note that ClickUp utilizes AI and machine learning technologies during the application review process to support human decision-making.