Director, Technical Program Management - Technical Solutions Operations

Datadog's Technical Solutions (TS) organization is one of the largest organizations in the company — spanning Sales Engineers, Technical Account Managers, Enterprise Customer Success Managers, Technical Support Engineers, and Solutions Architects who work with prospects and customers across every stage of their journey with Datadog. Technical Solutions Operations (TSO) exists to make that organization faster, smarter, and more scalable. We build the systems, analytics & programs that give TS teams more leverage — and we measure our success by the business outcomes we drive, not the projects we complete. The programs this team runs touch every function in TS, and the operating model you build will define how that scales. We're looking for a Director of Technical Program Management to lead the TSO Program Management team. This role sits at the intersection of strategy and execution: you'll own the programs that shape how TS operates at scale, lead a team of technical program managers, and serve as a peer to the Directors and VPs who run the teams you support. Your counterparts are leaders overseeing hundreds of customer-facing technical professionals, and your role is to successfully interface with each organization with proactive solutions on how your team can help them be more effective. This is a rare opportunity to lead a function where the output isn't a deliverable, it's organizational capability. If you want to build something that compounds across an entire organization, this is the role. 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 • Run the PMO as a business impact function. Own the PMO operating model end-to-end, including intake, prioritization, scoping, execution, and impact measurement — with every program directly linked to measurable business outcomes such as productivity gains, revenue influence, cost efficiency, or customer experience improvements. Establish a PMO operating standard that other TS leaders adopt as the benchmark. • Build capabilities that scale across TS, not point solutions. Build durable, cross-functional capabilities that drive business outcomes across every function in TS. Solve systemic problems with scalable solutions and operating models — not one-off fixes — and hold your team to the same standard. • Drive programs from alignment to impact. Establish clear scope, sequencing, ownership, and success metrics before execution begins. Hold your team to rigorous delivery standards and close every program with post-launch reporting that connects leverage created directly to business outcomes for partner teams. • Represent TSO in executive forums. Represent TSO in executive forums with Director and VP-level counterparts across TS. Come prepared with clear recommendations, framed trade-offs, and the ability to drive decisions — not surface issues. Own stakeholder relationships and outcomes and drive alignment across disparate teams. • Deploy AI to create operational leverage. Identify and build AI-enabled workflows that reduce friction across how programs are planned, communicated, and executed — for your team and for the TS functions you support. This is a core expectation, not a future initiative. You bring a clear point of view on where AI creates a genuine capability shift and you build toward it. • Develop the TPM team and raise the bar. Lead a team of senior Technical Program Managers delivering complex, concurrent initiatives across TS. Raise the bar for execution quality, stakeholder management, and accountability — and develop a team that operates independently and owns outcomes. • Build cross-functional relationships before you need them. Build cross-functional relationships across TS and adjacent functions before programs require it. Use influence, credibility, and direct engagement to drive alignment, resolve tension, and expand the reach and impact of TSO well beyond its own boundaries. Who You Are • 10+ years running complex, cross-functional programs at a senior level, with VPs and senior Directors as your primary stakeholders — ideally within a high-growth B2B SaaS go-to-market, customer-facing, or revenue operations organization • A systems builder with a track record of designing operating models, playbooks, and frameworks that other teams adopted as a reference standard • Autonomously executive-ready — decisive under ambiguity, composed under pressure, and capable of leading VP-level conversations without preparation coaching • Experienced applying AI as an operational tool, with a practical point of view on where it creates capability shifts — not just productivity gains • A developer of senior talent who raises the bar on what great program management looks like and builds teams that operate independently at a high standard • Outcome-oriented and metric-driven — you define success before work begins and hold yourself and your team accountable to delivering against it Preferred Experience • Experience supporting large-scale go-to-market or customer-facing technical organizations spanning sales engineering, post-sales, technical support, or solutions architecture • Familiarity with support operations platforms and the workflows they enable across technical teams • Experience designing org-wide AI-enabled capabilities in an operational context • Background in tooling strategy, workforce planning, or operational transformation at scale in a SaaS environment 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. Benefits and Growth: • New hire stock equity (RSUs) and employee stock purchase plan (ESPP) • Continuous professiona