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Director, Enterprise Sales

Datadog - United States - Hybrid - posted 2026-09-14

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Salary: USD 165,000 - 220,000 / annual

Datadog is seeking a Director of Enterprise Sales to lead and manage a high-performing team of Enterprise Sales Executives responsible for driving new business and expansion bookings through the full sales cycle. This is a hybrid role based in Michigan, Ohio, or Pennsylvania. You will manage, hire, train, and ramp a team of Enterprise Sales Executives while achieving annual Enterprise bookings quotas with monthly and quarterly targets. Your responsibilities include developing sales executives on key productivity metrics such as deal size, win rate, and forecast accuracy; coaching them through building executive relationships with Named Enterprise accounts and navigating complex negotiations. You will shape the go-to-market strategy and execution for your region, working collaboratively with Marketing, Product, and Success teams to build targeted messaging and customer journey mapping aligned with regional business needs. You'll conduct weekly forecast meetings and actively participate in and lead client and prospect meetings, engaging corporate resources as needed. Datadog is the leading observability and security platform for the AI era, providing unified visibility across technology stacks to manage complexity at scale. The company brings applications, infrastructure, data, models, and security into one place using AI to detect and resolve issues before they impact customers. Trusted by Fortune 500 companies and high-growth AI leaders globally, Datadog enables businesses to move faster with clarity and confidence. The role requires regular travel to client sites within your area and other regions using various modes of transportation (car, train, air) depending on business needs. QUALIFICATIONS: - Experienced in managing a high-performing Enterprise Sales team for a B2B technology company - 5+ years of overall Enterprise sales experience working with Fortune 1000 companies - Strong relationship builder with confidence in managing complex sales processes involving multiple stakeholders and negotiations based on business value, legal, and procurement considerations - Knowledgeable in selling to C-level executives in the IT space - Experienced in setting quotas and managing people against those quotas - Passionate about coaching others with a successful track record as an individual contributor; able to share relevant and complex closing experience with a growing team - Willingness to travel regularly as business needs require

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