Director, Sales Field Enablement - NYC

About Datadog:

Datadog is the world’s leading monitoring service for cloud-scale applications, bringing together data from servers, databases, tools and services to present a unified view of your entire stack. These capabilities are provided on a SaaS-based data analytics platform that enables Dev and Ops teams to work collaboratively to avoid downtime, resolve performance problems, and ensure that development and deployment cycles finish on time.

The team

Sales Enablement is an integral part of the GTM Enablement organization at Datadog -- a team responsible for empowering all Go-To-Market (GTM) teams to drive Datadog’s next phase of growth. We’re interdisciplinary thinkers leveraging diverse backgrounds in business development, education, management consulting, law, finance and business operations to build, deliver and optimize Datadog’s enablement programs. Our sales enablement function partners with teams across Datadog - from leaders to other GTM teams -  to ensure our company goals are met and our salespeople reach their potential.

The opportunity

Datadog is scaling rapidly, and we need world-class enablement to keep our go-to-market teams ahead of the curve. As our Director of Sales Enablement, you’ll lead a talented team of Field Enablement Managers who design and deliver training that powers our global Sales and Customer Success organizations.

In this role, you’ll partner with leaders across Curriculum & Strategy, Business Value, Sales, Customer Success, and Product Marketing to create programs that drive measurable impact in the field. But we’re looking for more than a training leader—you’ll be a visionary who pushes the team beyond “stand and deliver” workshops to become true business partners. You’ll empower the team to anticipate the needs of the field, prescribe data-driven solutions, and elevate performance at scale.

If you’re excited about shaping the future of enablement at a hypergrowth company—and raising the bar for what field enablement can deliver—we’d love to talk.

Responsibilities:

• Lead and build a high-performing team of sales and customer success trainers as they execute world-class enablement programs to the field

• Execute ongoing field training at Datadog: guide GTM teams through their learning journeys via sales kick off, quarterly business reviews, classroom sessions, e-learnings and other formats

• Spearhead the Field Enablement team’s transition from facilitators to data-driven business partners and coaches who are able to proactively identify GTM knowledge/performance gaps and deliver targeted enablement solutions

• Embed with our go-to-market teams and develop a clear understanding of the realities of selling Datadog in each region

• Partner with SMEs and the Curriculum & Strategy team to design engaging live training experiences and measure the business impact of our training programs

• Create one-to-one / one-to-few coaching programs that develop the most critical sales and sales leadership skills

• Be the voice of the field (sales and CS teams): represent their perspective through your understanding of their needs and their strengths and weaknesses as you interface with cross-functional teams

Qualifications:

• 8 years of work experience including at least 4 years in sales enablement, L&D or other equivalent experience teaching others 

• 3+ years of experience managing direct reports in highly complex / ambiguous environment

• You’ve led classroom style instruction in your career and helped develop a curriculum 

• You’re a great listener with a high EQ and an intrinsic drive to help people grow

• You have a strong aptitude for tying enablement programs to business impact

• Proven track record of building and maintaining scalable programs 

• Agile mindset: proven ability to iterate, build minimum viable “products” and improve

• Outstanding verbal and written communicator: you make the complex simple

• Experience presenting to and planning summits for hundreds of people 

Bonus points

• You’ve worked as a seller or customer-facing rep

• You’ve been a sales coach or an enablement business partner

• Experience at a high growth Software-as-a-Service or technology company

• Knowledge of DevOps or cloud technologies

• Experience teaching or using MEDDICC

• Experience building effective programs at our scale or greater

• Advanced degree in teaching or education