Regional Director - Enterprise Sales
Lead a team of Enterprise Sales Executives to drive new business and achieve sales targets in a hybrid work environment.
Posted by employer 3 days ago
First seen on Joblaze 3 days ago
Last verified on the company career page 7 hours ago
What you'll build
- Manage, hire, train and ramp a team of Enterprise Sales Executives
- Achieve annual Enterprise bookings quota
- Develop and manage productivity metrics for Sales Executives
- Coach Sales Executives on building executive relationships
- Shape the go-to market strategy for the region
Must have
- 5+ years of overall Enterprise sales experience
- Experience managing a high performing Enterprise Sales team
- Confident in managing complex sales processes
- Knowledgeable in selling to C-level executives
- Experience in setting quotas and managing people against those quotas
Nice to have
- Passionate about coaching others
- Successful track record as an individual contributor
Practical constraints
- Ability to travel to Tokyo approximately twice a month
- Ability to travel within Japan, including to the Osaka area
- Ability to travel internationally up to four times per year
Requirements
- Experience
- 5+ years
Not disclosed in this posting: compensation, visa sponsorship.
Benefits
Joblaze summary
The Regional Director of Enterprise Sales at Datadog is responsible for leading a team of Enterprise Sales Executives, focusing on driving new business and managing the full sales cycle. This role requires expertise in B2B technology sales, particularly with Fortune 1000 companies, and involves coaching team members on complex negotiations and relationship-building with C-level executives. Ideal candidates will have a strong background in managing sales teams and achieving quotas, along with a passion for mentoring others. Datadog emphasizes a collaborative office culture and offers a hybrid work model.
Joblaze insights
- Listed 3 days ago — first seen on Joblaze September 23, 2026. Last confirmed on Datadog's careers page September 26, 2026.
- This exact title is also open at 1 other location at Datadog: Osaka, Japan.
Quick facts
- Is the Regional Director - Enterprise Sales role remote?
- It's hybrid — Datadog expects some on-site time in Osaka, Japan.
- How much experience is required?
- At least 5 years of relevant experience for this Regional Director - Enterprise Sales role.
- Where is the role based?
- Datadog is hiring for this position in Osaka, Japan.
- What seniority level is this role?
- Datadog targets director candidates for this position.
- Is this full-time or contract?
- Full-time for this Regional Director - Enterprise Sales role at Datadog.
From the original posting
Our Director, Enterprise Sales will provide strategy, mentorship, and guidance for a team of Enterprise Sales Executives who are responsible for driving new business through the full sales cycle.
What You’ll Do:
- 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 through building executive relationships with Named Enterprise accounts in their territories and through complex Enterprise deals and negotiations
- 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 direct reports by participating and leading in client and prospect meetings. Engaging other corporate resources as required
Who You Are:
- Experienced 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
- Passionate about coaching others with a successful track record as an individual contributor and can share relevant and complex closing experience with a growing team
- Ability to travel to Tokyo approximately twice a month and work from the Tokyo office for several days per visit
- Ability to travel within Japan, including to the Osaka area, for customer meetings and other business needs
- Ability to travel internationally to the United States or within the APAC region up to four times per year for internal events and other business needs
Benefits and Growth:
- High income earning opportunities based on self performance
- New hire stock equity (RSU) and employee stock purchase plan (ESPP)
- Continuous professional development, product training, and career pathing
- Sales training in MEDDIC and Command of the Message
- Intra-departmental mentor and buddy program for in-house networking
- An inclusive company culture, opportunity to join our Community Guilds
- Generous and competitive medical benefits package
- Retirement savings match
- Pet adoption and insurance program
#LI-Hybrid
About Datadog:
Standard company text repeated across Datadog's postings is omitted here.