Regional Director, Enterprise Sales (CENTRAL)- Chicago

At ClickUp, we’re not just building software. We’re architecting the future of work! In a world overwhelmed by work sprawl, we saw a better way. That’s why we created the first truly converged AI workspace, unifying tasks, docs, chat, calendar, and enterprise search, all supercharged by context-driven AI, empowering millions of teams to break free from silos, reclaim their time, and unlock new levels of productivity. At ClickUp, you’ll have the opportunity to learn, use, and pioneer AI in ways that shape not only our product, but the future of work itself. Join us and be part of a bold, innovative team that’s redefining what’s possible! 🚀

You will work directly with sales leadership as a front-line problem solver and you’ll work hands-on to evolve a sales system based around product and demos into something rock solid that scales. We’re looking for a player-coach who remembers the hustle and can help triple our revenue in 2025.

Additionally, you will work closely with senior leaders across Growth, Marketing, Operations, and Product. At ClickUp, our teams are tightly connected, and if you need something developed in order to win a meaningful account, we can and will allocate resources to get it released.

We are not interested in aggressive or annoying sales tactics. Our secret sauce is helping people see the value of the solution we provide and stepping in to assist product-led growth.

MUST BE LOCATED IN CHICAGO AND WILLING TO COME INTO AN OFFICE 3-4 DAYS A WEEK.

The Role:

• Manage a pod of at least 5 account executives.

• Coach, train, and support reps in closing deals and driving revenue growth.

• Serve as a player-coach on calls to train new reps and help established reps constantly improve.

• Motivate all team members to go above and beyond for customers.

• Construct a fun, high-energy environment where reps love coming to work and feel as if they’re being developed towards their fullest potential.

• Prioritize customer experience over making the sale, lead by example as a manager, and monitor adherence to sales policies and practices across your reports.

Qualifications:

• 3+ years of full-cycle sales experience in SaaS and 3+ years of ENT sales management experience

• Very strong understanding of selling into Upmarket segments in an expansion focused sales motion. 

• Demonstrated ability to develop and implement effective sales strategies that drive revenue growth

• Experience in managing and scaling sales teams, with a focus on fostering a high-performance culture

• Strong analytical skills to assess sales performance metrics and make data-driven decisions

• Excellent communication and interpersonal skills, with the ability to build strong relationships with clients and internal stakeholders

• Proven track record of achieving and exceeding sales targets in a competitive environment

• Ability to adapt to a fast-paced, dynamic work environment and manage multiple priorities effectively

• Experience with CRM software and sales analytics tools to track and optimize sales processes.

• Strong leadership skills with the ability to inspire and motivate a team towards achieving common goals.

#LI-HYBRID

#LI-JMS

Unsure if you meet all the qualifications of this job description but are deeply excited about the role? We hire based on ambition, grit, and a passion for improving the way people work. If you think ClickUp is the company for you, we encourage you to apply!

At ClickUp, we assess every candidate based on the potential impact they can have. We hire the best people for the job and support each person’s journey to build their boldest career.

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.

Privacy Notice

ClickUp collects and processes personal data in accordance with applicable data protection laws. You can find further details by viewing our Global Candidate Privacy Notice.

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.

Fraud Alert

ClickUp Talent Acquisition will only initiate contact via an @clickup.com email or through our official careers portal on clickup.com. We will never request fees, payments, or sensitive personal information. Please disregard any offers received outside these channels and report them to [email protected].

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].