AI-Driven TPM for Complex Cross-Functional Programs

Triwill Group; New York (NY); Hybrid; USD 146,000 - 182,000; Full time

Benefits offered by this job

Stock equity (RSUs)

Employee stock purchase plan (ESPP)

Mentor program

Career development and training

Inclusive culture and team summits

Job summary

Datadog seeks a Technical Program Manager to own large cross-functional programs across engineering, product, and business units in a fast-growing tech environment. You will apply technical depth in observability, infrastructure, data platforms, and AI/ML systems to move high-priority initiatives forward with minimal supervision.

You will build AI-powered automation, surface risks early, and drive execution across teams while maintaining senior executive visibility through KPI tracking and

Qualifications

• 3+ years of technical program management at a high-growth technology company.
• Demonstrated ability to drive large, ambiguous, cross-functional programs to completion with minimal direction.
• Engineering credibility earned through hands-on experience with technically complex domains — observability, infrastructure, data platforms, or AI/ML systems including model training pipelines, ML infrastructure, and GPU compute.
• Track record of earning trust with senior engineering and product leadership - not through title, through judgment.
• Strong written and verbal communication; comfortable owning the narrative at VP+ levels.
• Active AI practitioner, you use AI tools in your daily work and can demonstrate how they’ve changed your leverage.
• You have built something, a tool, a template, an automated workflow, that other people use

Responsibilities

• Own large cross-functional programs spanning multiple engineering orgs, product, and business functions
• Proactively surface systemic risks, cross-pod dependencies, and organizational friction before they become escalations
• Build and maintain SVP-level visibility through tracked KPIs on Datadog’s highest-priority initiatives
• Uses technical credibility, trusted relationships, and product domain expertise to bridge the gaps between functions where misalignment is expensive
• Identify repeatable program archetypes and engineer the lifecycle end-to-end with AI solutions; the goal is to make the program run itself
• Build automation that reduces the need for coordination, eliminating program overhead so engineers and PMs spend time only on work requiring human judgment
• Contribute to the TPM toolkit: AI-powered risk synthesis, dependency tracking, stakeholder mapping, and program templates
• Drive the shift from manual coordination to self-executing program infrastructure
• Lead programs across four archetypes: deep technical, large cross-functional, product delivery, and operational
• Accelerate alignment by removing friction and overhead, not by adding process.
• Hold the judgment call on when to elevate, when to slow down, when a technical decision has organizational implications
• Own outcomes, not activities - your value is measured by what ships and what never had the chance to become a problem

Skills

Technical program management

AI systems literacy

Cross-functional leadership

Communication (written)

Active AI practitioner

Automation/ tooling

Architectural judgment

Job description

Datadog seeks a Technical Program Manager to own large cross-functional programs across engineering, product, and business units in a fast-growing tech environment. You will apply technical depth in observability, infrastructure, data platforms, and AI/ML systems to move high-priority initiatives forward with minimal supervision.

You will build AI-powered automation, surface risks early, and drive execution across teams while maintaining senior executive visibility through KPI tracking and