Datadog Hiring: Director, Enterprise Sales (Remote, Headquarters Texas)

Datadog is recruiting a Director of Enterprise Sales to provide strategy, mentorship, and hands-on leadership for a team of Enterprise Sales Executives. The team's core mission is to drive new business and account expansion across Named Enterprise accounts through the full sales cycle. The company emphasizes office culture and uses a hybrid workplace model intended to balance in-person collaboration with remote work.

This is a frontline sales leadership role with responsibility for both people and revenue outcomes. The Director will hire, train, and ramp Enterprise Sales Executives and hold the team to an annual Enterprise bookings quota with defined monthly and quarterly targets. Daily and weekly activities include conducting forecast meetings, coaching on deal execution, and actively participating in client and prospect meetings as needed.

Performance focus and management metrics

The role measures and improves core productivity metrics for Sales Executives: deal size, win rate, and forecast accuracy. The Director is expected to teach reps how to guide customers through proactive sales cycles, build executive relationships within Named Enterprise accounts, and navigate complex enterprise negotiations including pricing discussions.

Datadog expects the Director to work collaboratively with Marketing, Product, and Customer Success. Specific responsibilities include developing targeted messaging and collateral, mapping customer journeys that align to regional business needs, and shaping regional go-to-market strategy and execution. The Director will also engage other corporate resources when deals require additional technical, product, or executive support.

The posting specifies an experienced sales manager with a history of leading high-performing Enterprise Sales teams in B2B technology. Candidates should have a minimum of five years in Enterprise sales working with Fortune 1000 companies and be comfortable managing complex sales processes involving multiple stakeholders and negotiations. The role requires strong relationship-building skills and confidence in handling enterprise-level deal dynamics.

The job lists headquarters in Texas, USA and notes the role is remote. Datadog describes itself as operating a hybrid workplace to preserve office-driven collaboration while offering flexibility for individuals to create their preferred work-life harmony.

Apply if you have proven experience scaling enterprise sales teams in B2B tech, track record working with large enterprise customers, and appetite for a role that combines management, strategy, and active deal support. The role is suited to leaders who want to influence go-to-market execution while remaining close to customer-facing activity.