Senior Program Manager, Sales Enablement

About this role

Our GTM Enablement team plays a critical role in helping Datadog’s Sales and Customer Success teams succeed by equipping them with the right skills, knowledge, and tools at the right time. We partner closely with teams across Sales, Customer Success, Product Marketing, Strategy & Operations and more to ensure enablement programs translate into real performance in the field.

The Program Management team within Sales Enablement is a group of interdisciplinary thinkers leveraging diverse business backgrounds in engineering, education, management consulting, business operations (and more!) to define, manage and measure Datadog’s global go to market motion. We solve complex, systemic challenges that impact go-to-market effectiveness by diagnosing root causes, whether behavioral, skills-based, or structural, and shaping the strategic solutions that resolve them. We partner closely with our Sales Enablement stakeholders across Curriculum, Field Enablement, Operations, and more to deliver on measurable results and operate as one unified enablement team.

As a Senior Program Manager on the Sales Enablement Program Management team, you will design, plan, and execute complex, global, cross-functional programs that change how our Go-to-Market (GTM) teams operate at a systems level. You will own the end-to-end enablement process for the programs and stakeholder relationships you’re responsible for: diagnosing the gap, gathering field evidence, building a multi-faceted strategy (not just a content solution), partnering across teams to deliver the experience, and reporting business impact to Sales and Customer Success leadership.

This is a high-ownership role for someone who moves quickly, thinks strategically and creatively, and is equally comfortable analyzing hard data and reading what’s happening on the ground. You’ll drive adoption at scale with limited guidance, influence senior stakeholders without positional authority, and help shape how the Program Management function operates as it matures. Over time, the work spans segment-aligned program ownership as well as transformative, cross-functional initiatives such as our sales methodology, GTM playbooks, tooling, process and AI enablement.

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:

• Own assigned enablement programs end-to-end - develop the strategy and project plans, set success criteria, manage timelines and milestones, and drive delivery on time and to enablement standards

• Diagnose performance gaps for the audiences you support and translate field findings into a multi-faceted strategy that spans curriculum, field, systems, and process - not content alone

• Partner closely with your Sales Enablement stakeholders across Curriculum, Field Enablement, Operations, and more to deliver on measurable results and operate as one unified enablement team

• Drive relationships with senior stakeholders across Sales, Customer Success, Strategy & Operations, Product Marketing, Legal, People Team, and other GTM partners to negotiate objectives, deliverables, and delivery methods on global programs

• Lead cross-functional stakeholder teams to develop and pilot change management programs, and ensure effective adoption at scale

• Play a leading role in Datadog's broader GTM transformation, contributing to cross-functional initiatives such as sales methodology, GTM playbooks, tooling, and process enablement that reshape how our go-to-market teams operate at scale

• Design and analyze metrics to measure change adoption and business impact; build and pull reports and dashboards (e.g., Salesforce, Tableau/Metabase) and present findings to leadership, iterating on programs to ensure lasting change

• Maintain a pulse on regional and segment needs to identify opportunities for new or updated programs; partner with Curriculum and Field teams to integrate workflow changes into ongoing enablement experiences

• Tell the impact story - connect program outcomes to seller and CSM productivity and deliver clear read-outs to Sales and CS leadership

• Mentor and develop junior Program Management ICs, providing structured feedback on program design and stakeholder management

• Demonstrate AI Fluency by designing AI-enhanced program tracking and stakeholder reporting, using AI to synthesize field feedback and build data stories for leadership, and helping define team standards for responsible AI use in program management workflows

Who You Are:

• You have 6+ years of experience in program management, change management, sales enablement, strategy & operations, systems design, or a related field, with a track record of measurable adoption outcomes. You thrive at connecting disparate dots and making meaning out of various inputs.

• You have deep expertise in change management and program design, and have managed complex, multi-stakeholder programs across global teams with limited guidance

• You are highly data-driven across both quantitative and qualitative inputs - comfortable analyzing business metrics to identify performance gaps and measure impact, as well as running surveys, in-field investigations, and interviews. Experience with tools such as Salesforce and Tableau/Metabase is a plus

• You excel at stakeholder and project management, building alignment across cross-functional teams and driving adoption without formal authority

• You are a clear and compelling communicator who can simplify complexity, influence senior leaders, and inspire behavior change at scale

• You bring familiarity with sales and CS workflows, methodologies, processes, and tools, and understand how they connect to seller productivity and customer value (working knowledge of frameworks such as FETCH and MEDDICC is a plus)

• Change management certification such as PROSC

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