Senior Training Associate, Technical Solutions

As part of Datadog’s Go-to-Market Enablement department, the Technical Solutions (TS) Enablement team delivers ongoing education and scalable learning experiences for our internal product experts—including Sales Engineers, Support Engineers, and Technical Account Managers. Specifically, the TS Field Enablement team leads high-impact, live programs designed to drive technical proficiency and consistent execution across our global technical teams.

The Opportunity

As a Senior Training Associate, you will serve as a specialist who bridges the gap between enablement operations and live program delivery. You will be responsible for ensuring our global programs work at scale while beginning to step into a facilitation role. This is an ideal role for someone with a strong operational foundation who is looking to grow into a training and delivery specialist. This role is designed to set you up for long-term growth — equipping you with the skills, relationships, and field context to take on greater ownership of enablement delivery over time.

At Datadog, we place value in our office culture - the relationships and collaboration it builds and the creativity it brings to the table. We operate as a hybrid workplace to ensure our Datadogs can create a work-life harmony that best fits them.

What You’ll Do

Execute and manage end-to-end logistics for training programs, including speaker scheduling, training room coordination, enrollment workflows, and train-the-trainer logistics. Coordinate with People Operations and IT to ensure seamless system integration across all global field programs.

Manage communication for field programs, including Slack channels, resource pages, and program updates, to keep stakeholders and learners aligned.

Co-facilitate training sessions and lead specific modules, such as new hire onboarding, to support global delivery.

Work with Technical Solutions teams to understand day-to-day workflows, identify real-world training gaps, and align enablement initiatives to team needs.

Host recurring enablement calls and technical product deep-dive sessions, serving as a key point of contact between field teams and product owners to ensure technical teams stay current on platform updates and best practices.

Provide field observations and learner feedback to help improve training materials and program delivery.

Manage post-training surveys and reporting on program effectiveness, using learner feedback and shadowing observations to recommend improvements to the TS enablement strategy.

Who You Are

You have 3+ years of experience in enablement, operations, or a customer-facing technical role.

You can independently manage multi-step program logistics—scheduling, communications, stakeholder coordination, and system updates—with minimal oversight.

You are proficient in Google Workspace and have hands-on experience with enablement and collaboration tools such as Docebo (LMS), Confluence, and Slack.

You can interpret program metrics—survey results, completion rates, attendance trends—and translate them into actionable recommendations.

You have strong written and verbal communication skills, with the ability to craft professional communications for a global audience.

You take initiative to support colleagues' professional development and are motivated by helping technical teams improve how they work.

You are interested in deepening your knowledge of the Datadog platform and observability best practices.

You are fluent in English, both written and spoken, with the ability to communicate effectively across global teams.

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, we encourage you to apply.

Bonus Points

Experience in a SaaS or fast-moving technology environment, particularly within a Go-to-Market organisation.

Familiarity with Datadog's platform or comparable o