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Datadog is seeking a Regional Director of Enterprise Sales to lead a team of Account Executives in Osaka, Japan, driving full-cycle new business and expansion within existing accounts. This is a people-management role overseeing recruitment, onboarding, coaching, and performance management of enterprise sales professionals.
Key Responsibilities:
- Manage, hire, train, and onboard an Account Executive team focused on new enterprise contracts and customer expansion
- Achieve monthly and quarterly targets, driving the enterprise team toward annual contract value goals
- Monitor and support Account Executive growth using productivity metrics including deal size, win rates, and forecast accuracy
- Coach team members through complex enterprise negotiations and C-level executive relationship building
- Develop and execute Go-to-Market strategy for the assigned region
- Collaborate with Marketing, Product, and Customer Success to create tailored messaging, promotional materials, and customer journey maps
- Conduct weekly forecast meetings
- Participate in prospect and customer meetings, lead deals, and support direct reports; leverage internal resources as needed
Datadog is a leading observability and security platform trusted by Fortune 500 companies and high-growth AI leaders. The company provides unified visibility across technology stacks to manage complexity at scale, combining applications, infrastructure, data, models, and security in one platform.
The role is hybrid, based in Osaka with approximately bi-monthly travel to Tokyo (several days per trip), domestic travel within Japan for customer engagements, and up to four annual trips to the US or APAC region for company events.
Requirements:
- Proven experience leading high-performing enterprise sales teams at B2B technology companies
- 5+ years of enterprise sales experience with demonstrated success building relationships with Fortune 1000 companies
- Expertise in value-based pricing negotiations and managing complex sales processes involving multiple stakeholders (legal, procurement, etc.)
- Deep knowledge of selling to C-level IT executives
- Experience setting sales targets and managing team members toward goal achievement
- Passion for coaching based on personal IC success; ability to share relevant closing experience with growing teams
- Ability to travel to Tokyo approximately twice monthly for multi-day office visits
- Flexibility for domestic travel within Japan for customer meetings
- Availability for up to four annual international trips (US or APAC) for company events
