Leadership Training Manager

Datadog-posted 2 days ago

Full-time • Manager

Hybrid • New York, NY

1,001-5,000 employees

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Datadog is seeking a Leadership Training Manager to design, deliver, and scale impactful learning experiences that enable our employees to grow and thrive. This role includes live facilitation, program management, curriculum development, content design, impact and success measurement, and ongoing innovation. Your primary focus will be upskilling manager populations, including experienced and senior people leaders. You will also be the program owner for our in-house inclusion training, proactively tracking outcomes and driving the direction of this initiative while regularly delivering live sessions to Datadogs at all levels and roles. You will support additional projects, programs, and initiatives that advance the goals of our team and organization. You’ll balance ongoing facilitation of high-impact manager, inclusivity, and other skill workshops along with the program management elements: refining curriculum, leveraging new tools and methodologies (including AI and microlearning), and ensuring programs adapt to meet evolving business needs. 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.

Facilitate dynamic in-person and virtual workshops on manager development, people leadership, inclusivity, and other growth topics.
Lead productive conversations about people management with audiences up to senior leadership (VP+), driving deep learning and lasting behavior change.
Create safe, inclusive spaces that engage and resonate with employees across different functions and global regions (AMER, EMEA, APAC).
Travel to different Datadog offices up to 30% of the time to deliver workshops – primarily domestic US, but also internationally as needed.
Manage learning programs end-to-end – guide the overall strategy and direction, drive decisions on content and delivery, proactively track outcomes, communicate with stakeholders, and make ongoing enhancements to ensure programs meet evolving business needs.
Partner cross-functionally to execute our programs effectively and pilot new content and modalities that scale and generate impact.
Use data insights to evaluate program effectiveness, propose meaningful improvements, align with stakeholders, and implement solutions.

10+ years of relevant career experience, including 6-8 years supporting people managers within corporate or high-growth environments through live facilitation, executive coaching, or similar
Strong presence and adaptability as a facilitator across both in-person and virtual environments, with a track record of engaging audiences from various roles, levels, and geographies.
Demonstrated ability to own programs end-to-end – designing programs, developing content, delivering, measuring outcomes, and iterating for improvement.
Excellent communication and stakeholder management skills, with the ability to influence across levels, including senior leadership.
Ability to use various learning systems (e.g., LMS, content authoring platforms, AI tools) and eagerness to explore emerging learning technologies.
Willingness and ability to travel up to 30% of the time – primarily domestic US, but also internationally as needed.

Generous and competitive global benefits
New hire stock equity (RSUs) and employee stock purchase plan
Continuous career development and pathing opportunities
Product training to develop an in-depth understanding of our product and space
Best in breed onboarding
Internal mentor and buddy program cross-departmentally
Friendly and inclusive workplace culture
Benefits and Growth listed above may vary based on the country of your employment and the nature of your employment with Datadog.

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