Job Overview
Location
United States of America
Job Type
Full-time
Category
Sales
Date Posted
April 3, 2026
Full Job Description
📋 Description
- • As Regional Director, Enterprise Sales (CENTRAL) based in Chicago, you will lead and scale a high-performing sales pod of at least five Account Executives, directly contributing to ClickUp’s mission to triple revenue in 2025 by transforming how teams work through its AI-powered converged workspace.
- • You will serve as a player-coach, actively participating in sales calls to model best practices, train new hires, and continuously elevate the performance of established reps through real-time feedback and strategic deal coaching.
- • Your day-to-day will involve managing full-cycle sales activities including pipeline development, forecasting, deal strategy, and closing complex enterprise opportunities while ensuring alignment with ClickUp’s product-led growth philosophy and customer-centric values.
- • You will partner closely with senior leaders across Growth, Marketing, Operations, and Product to secure cross-functional resources—such as custom demos, technical enablement, or tailored content—to win strategic accounts and accelerate deal velocity.
- • A core responsibility is fostering a fun, high-energy, and psychologically safe team culture where reps feel motivated, developed, and empowered to exceed their potential, prioritizing long-term customer success over short-term transactional wins.
- • You will enforce sales policies and best practices across your team, leveraging CRM and analytics tools to monitor performance, identify coaching opportunities, and make data-driven decisions that optimize conversion rates, win rates, and quota attainment.
- • Beyond execution, you will help evolve ClickUp’s sales systems from a product/demo-led foundation into a scalable, repeatable enterprise engine—documenting playbooks, refining processes, and embedding learnings to support future growth.
- • This role offers the unique opportunity to shape the future of work by selling a platform that unifies tasks, docs, chat, calendar, and search with AI, directly impacting how millions of teams collaborate and reclaim productivity.
- • You will grow as a sales leader by operating at the intersection of strategy and execution, gaining exposure to senior leadership, cross-functional initiatives, and the inner workings of a high-growth SaaS company redefining enterprise software.
🎯 Requirements
- • 3+ years of full-cycle sales experience in SaaS
- • 3+ years of enterprise sales management experience
- • Proven track record of selling into upmarket segments with an expansion-focused motion
- • Demonstrated ability to develop and execute sales strategies that drive measurable revenue growth
- • Experience managing and scaling sales teams while building a high-performance, customer-obsessed culture
- • Strong analytical skills to interpret sales metrics and drive data-informed decisions
- • Excellent communication and relationship-building abilities with clients and internal stakeholders
- • Proficiency with CRM platforms and sales analytics tools (e.g., Salesforce, Outreach, Gong)
- • Strong leadership and motivational skills to inspire teams toward shared goals
- • Ability to thrive in a fast-paced, dynamic environment and manage competing priorities effectively
🏖️ Benefits
- • Opportunity to work on a mission-driven product transforming the future of work through AI
- • Hybrid work model requiring 3–4 days per week in the Chicago office
- • Access to professional growth and leadership development within a rapidly scaling SaaS leader
- • Collaborative, innovative culture with tight alignment across sales, product, marketing, and operations
- • Resources allocated to support winning strategic accounts (e.g., product, engineering, marketing support)
- • Exposure to senior leadership and cross-functional initiatives that accelerate career impact
- • Commitment to equity, inclusion, and equal opportunity in hiring and advancement
- • Support for bold career growth through ambition, grit, and passion—not just checklist qualifications
Skills & Technologies
Go
Hybrid
About Mango Technologies, Inc.
ClickUp is a San Diego-based productivity platform that unifies tasks, documents, goals, chat, and whiteboards in one cloud workspace. Founded in 2017, the company serves individuals, startups, and large enterprises seeking to replace scattered tools with a single, customizable hub. Its feature set includes hierarchical task management, real-time collaboration, time tracking, reporting dashboards, and hundreds of pre-built templates and integrations. ClickUp targets teams in software development, marketing, and operations that need to plan, execute, and monitor work without switching applications.
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