Sr Technical Program Manager (TS Systems) - Datadog : Job Details

New York, New York, USA; San Francisco, California, USA; Boston, Massachusetts, USA

We are seeking a highly motivated and experienced Senior Technical Program Manager (AI) to lead the design and deployment of AI/ML-driven solutions across our TS teams. Datadog's TS org is composed of 1000+ customer-facing technical experts around the world from Sales Engineers, Technical Account Managers, Support Engineers, and Solution Architects who work with prospects and customers across their journey with Datadog to deliver outstanding customer experiences and drive growth through rapid product adoption.

As a TPM on our Technical Solutions Operations (TS Ops) team, you will serve as a multiplier for the TS Org by identifying and implementing cutting-edge AI/ML tools and workflows that streamline and elevate customer experience. You will play a pivotal role in evaluating both internal and external AI solutions, overseeing automation initiatives, and ensuring data-driven decisions shape the next generation of AI-driven processes for Datadog's technical customer-facing teams. By partnering closely with Engineering, Data & Analytics, Vendor Teams, and TS across Datadog, you will help ensure our operations are robust, well-integrated, and prepared to scale. Additionally, you will stay attuned to business priorities, product investments, and emerging AI technologies, making certain that the AI solutions we rely on evolve in lockstep with Datadog's growth.

• Program Ownership: Define and execute an AI & Automation roadmap, enabling Datadog's Sales Engineers, Technical Account Managers, Support Engineers, and Solution Architects teams to scale effectively and deliver superior customer experiences.
• Solution Evaluation & Implementation: Identify and evaluate internal AI solutions (developed by Datadog engineering) and external AI vendor platforms for potential adoption, leading end-to-end development & deployment of selected technologies.
• Cross-Functional Collaboration: Work closely with TS leadership, and data engineering teams to align AI initiatives with broader organizational needs, ensuring solutions address real-world technical use cases.
• Operational Excellence: Oversee the full program lifecycle—from use-case discovery, requirements gathering, and POCs to change management, training, and continued optimization of AI-driven workflows.
• Impact Measurement: Define metrics and key performance indicators (KPIs) to quantify the effectiveness of AI & Automation initiatives, leveraging data insights to refine strategies and demonstrate ROI.
• Stakeholder Communication: Provide regular updates on progress, outcomes, and risks to senior leaders; proactively identify and mitigate blockers to maintain momentum.
• Thought Leadership: Keep up-to-date with emerging AI trends and technologies, introducing best practices and frameworks that enhance Datadog's AI-driven capabilities.

• Customer & Business Mindset: You continually focus on how AI can enhance customer outcomes and drive measurable business results across technical teams.
• AI & ML Fluency: You have a solid grasp of AI/ML principles (e.g., predictive models, natural language processing, generative AI) and know how to apply them to business processes.
• Data-Driven: You excel at turning insights into action, using quantitative and qualitative data to guide decisions and refine execution.
• Clear Communicator: You convey complex technical ideas in a concise way, adapting your message for diverse audiences—including product leads, senior executives, and technical specialists.
• Collaborative & Influential: You forge strong partnerships across organizational lines and are adept at influencing without direct authority to align teams on shared goals.
• Growth-Oriented: You thrive in a dynamic environment, continuously seeking ways to improve processes, learn new technologies, and evolve existing solutions.
• Proven Technical PM Experience: You have 5+ years of relevant experience leading complex cross-functional programs in a SaaS or similarly technical space, particularly around AI or automation.

• Technical Background: Bachelor's degree or equivalent in Computer Science, Engineering, or related field—or commensurate industry experience.
• Complex Program Delivery: Demonstrated success in managing multiple high-impact initiatives involving diverse technical stakeholders and deliverables, especially around AI/ML adoption.
• AI Vendor Management & Tool Evaluations: Comfortable overseeing evaluations, negotiations, and implementations of AI technology providers.
• Metrics & Analytics: Strong capability in defining success metrics, analyzing data, and delivering insights that guide iterative improvements and inform strategic decision-making.
• Systems & Process Automation: Experience with ticketing systems, workflow automation, or similar platforms is beneficial for translating AI solutions into tangible process improvements.
• Influence at Scale: Track record of collaborating with senior-level stakeholders to unify teams, drive adoption, and foster a culture of innovation in a high-growth global environment.

Benefits and Growth:

• Generous and competitive global and US 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

Datadog offers a competitive salary and equity package, and may include variable compensation. Actual compensation is based on factors such as the candidate's skills, qualifications, and experience.