Field Enablement Manager, Sales Enablement

WinsAbove; New York, Northern (NY, KY); Hybrid; USD 86,000 - 115,000; Full time

Benefits offered by this job

Benefits package

RSUs (stock)

Career development

Onboarding program

Mentor program

Inclusive workplace culture

Job summary

Datadog is seeking a Field Enablement Manager based in NYC to drive onboarding and ongoing enablement for Sales and Customer Success in AMER. You’ll partner with sales leaders to tailor global programs to regional needs and accelerate ramp for new hires and leaders.

You will deliver live and virtual trainings, manage certifications, gather field feedback, and collaborate with Curriculum, Program Management, and Operations to improve content. Travel ~25% across AMER.

Qualifications

• 3-5 years in sales enablement or related GTM role.
• Experience delivering live and virtual training to senior audiences.
• Familiarity with MEDDICC, Command of the Message, Challenger, Sandler, or similar frameworks.
• Ability to use performance data and field feedback to inform enablement decisions.
• Willingness to travel ~25% across AMER.

Responsibilities

• Deliver engaging live and virtual enablement sessions for global Sales and Customer Success teams, including onboarding, ongoing training, and reinforcement programs.
• Administer program certifications - score and evaluate submissions against established rubrics and provide structured feedback.
• Conduct ongoing field listening (shadows, 1:1s, syncs with first-line leaders) to identify business needs and share insights with the enablement team.
• Lead reinforcement and coaching to drive post-program adoption with measurable behavior changes in real customer scenarios.
• Partner with Curriculum, Program Management, and Operations to share field insights and co-build content; train first-line leaders as needed.
• Use AI tools to accelerate delivery and reinforce learnings across teams.

Skills

Field enablement

Sales enablement

Training delivery

Facilitation

AI tools

Tools

Asana

Job description

The Opportunity:

Datadog continues to grow at a rapid rate, and with this exciting growth, our onboarding and ongoing enablement programs are also increasing in scale and complexity. This position is part of a dynamic Field Enablement team responsible for delivering onboarding and ongoing enablement training and programs for all of our Sales and Customer Success teams in AMER.

You’ll serve as a trusted partner to Sales leaders, adapting global programs to the realities of the AMER motions while staying tightly aligned with our global Field Enablement organization.

This role is ideal for someone who thrives operating independently, builds strong relationships in the field, and enjoys adapting enablement programs to meet the needs of fast-growing sales teams.

As a Field Enablement Manager in NYC, you’ll be central to onboarding our global GTM Sales and Customer Success new hires, both ICs and leaders, setting the foundation for their success from day one. You’ll help accelerate ramp, build seller confidence, and enable sales teams to succeed with customers across one of Datadog’s fastest-growing and most complex regions.

What You’ll Do:

• Deliver engaging live and virtual enablement sessions for global Sales and Customer Success teams, including onboarding, ongoing training, and reinforcement programs.
• Administer program certifications - score and evaluate submissions against established rubrics and provide structured feedback.
• Conduct ongoing field listening (shadows, 1:1s, syncs with first-line leaders) to maintain a strong pulse on business needs, gaps, and strengths across AMER markets; share insights with the broader enablement team to shape programs and priorities.
• Lead reinforcement and coaching to drive post-program adoption, including designing activities (role plays, deal clinics, skill practice sessions) that connect training to measurable behavior change in real, complex customer scenarios.
• Partner with Curriculum, Program Management, and Operations to share field insights and pilot or co-build content, and work closely with first-line Sales leaders to build trusted relationships, diagnose challenges, and deliver ad hoc training in response to emerging needs.
• Use AI tools to accelerate delivery and reinforcement - including synthesizing field feedback and surfacing patterns - and model effective AI use for the teams you train.

Who You Are:

• 3-5 years of experience in sales enablement, field enablement, training, or a related GTM role, with a proven delivery track record supporting Sales and/or Customer Success teams in a SaaS or technology environment.
• Strong facilitator with experience delivering engaging live and virtual training sessions to senior, sophisticated audiences, and familiarity with sales methodologies/frameworks such as MEDDICC, Command of the Message, Challenger, Sandler, etc. (certification a plus).
• Strong business acumen and comfort using performance data, field feedback, and qualitative insights to inform enablement decisions; experience with Asana or similar project management tools is a plus.
• Foundational understanding of Datadog and/or the broader technology industry, including foundational knowledge of Datadog’s core product pillars (Infrastructure, APM, Logs) and the ability to connect product capabilities to customer value.
• Highly collaborative and relationship-oriented — you build trust quickly with sellers, managers, and cross-functional partners.
• Organized, adaptable, and comfortable operating independently across a large, diverse region.
• Willing and able to travel approximately 25% across AMER.

Datadog values people from all walks of life. We understand not everyone will meet all the above qualifications on day one. That's okay. If you’re passionate about technology and want to grow your skills.

Benefits & Growth:

• Generous and competitive benefits package
• New hire stock equity (RSUs) and employee stock purchase plan
• Continuous career development and pathing opportunities
• Employee-focused best in class onboarding
• Internal mentor and cross‑departmental buddy program
• Friendly and inclusive workplace culture

#LI-Hybrid

The reasonably estimated yearly salary for this role at Datadog is: $86,000 - $115,000 USD

About Datadog:

Datadog is the leading observability and security platform for the AI era, providing businesses with unified visibility across the technology stack to manage complexity at scale. It brings applications, infrastructure, data, models, and security into one place, using AI to detect and resolve issues before they impact customers. Trusted globally by Fortune 500 companies and high-growth AI leaders, Datadog enables businesses to move faster with clarity and confidence. Learn more about #DatadogLife on Instagram, LinkedIn, and Datadog Learning Center.

Equal Opportunity at Datadog:

Datadog is proud to offer equal employment opportunity to everyone regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, veteran status, and other characteristics protected by law. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. Here are our Candidate Legal Notices for your reference.

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