Enterprise Sales Leader: Strategy, Growth & Coaching

Xapply; Northern (KY); Hybrid; USD 165,000 - 220,000; Full time

Benefits offered by this job

RSU stock equity

ESPP

Professional development

MEDDIC training

Mentor program

Inclusive culture

Medical benefits

401(k) match

Pet adoption

Job summary

Datadog is seeking a Director of Enterprise Sales to lead a high-performing team responsible for new and expansion bookings within Fortune 1000 accounts. This role demands strategic leadership, hands-on coaching, and the ability to drive regional GTM execution across marketing, product, and customer success.

You will manage hiring, training, and ramping a team of Enterprise Sales Executives, while coaching them on executive relationships, complex negotiations, and quota attainment.

Qualifications

• Experience in managing a high performing Enterprise Sales team for a B2B technology company.
• A strong relationship builder with 5+ years of overall Enterprise sales experience working with Fortune 1000 companies
• Confident in managing complex sales processes with multiple stakeholders and negotiations with pricing based on business value, legal and procurement
• Knowledgeable in selling to C-level executives in the IT space
• Experienced in setting quotas and managing people against those quotas
• 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

Responsibilities

• Manage, hire, train and ramp a team of Enterprise Sales Executives responsible for new and expansion bookings
• Achieve annual Enterprise bookings quota with monthly and quarterly targets
• Develop and manage Enterprise Sales Executives on productivity metrics such as deal size, win rate, and forecast accuracy as well as how to lead a customer through a proactive sales cycle
• Coach Sales Executives in building executive relationships with Named Enterprise accounts and through complex Enterprise deals
• Shape the direction of the go-to market strategy and execution for your region
• Work collaboratively with Marketing, Product and Success to build targeted messaging and collateral, and mapping a customer journey for the specific business needs of your region
• Conduct weekly forecast meetings
• Support reports by leading client and prospect meetings and coordinating resources

Job description

Datadog is seeking a Director of Enterprise Sales to lead a high-performing team responsible for new and expansion bookings within Fortune 1000 accounts. This role demands strategic leadership, hands-on coaching, and the ability to drive regional GTM execution across marketing, product, and customer success.

You will manage hiring, training, and ramping a team of Enterprise Sales Executives, while coaching them on executive relationships, complex negotiations, and quota attainment.