Sr Director, Enterprise AI

Your role at Dynatrace

The Senior Director of Enterprise AI is accountable for defining, governing, and scaling Dynatrace's enterprise AI strategy to drive measurable productivity, operational efficiency, and competitive advantage across the organization. This role operates at the intersection of business strategy, applied AI, and organizational capability, translating a rapidly evolving technology landscape into a clear, enterprise-wide AI agenda with multi-year impact.  

Enterprise AI Strategy and Roadmap

• Partner with the VP of AI, Data & Collaboration and executive stakeholders to define, refine, and operationalize Dynatrace’s enterprise AI strategy, ensuring alignment with company priorities and measurable business outcomes.


• Develop a forward-looking perspective on generative AI, agentic systems, and workflow automation, translating market and technology shifts into practical strategic direction for the enterprise.


• Own the enterprise AI roadmap by identifying, prioritizing, and sequencing initiatives across Operations, Sales, Finance, HR, Legal, Marketing, and IT based on business value, feasibility, and risk.


• Lead portfolio-level build, buy, and partner decisions by evaluating SaaS vendors, platform integrations such as ServiceNow, Salesforce, and SAP, and custom-build trade-offs; bringing well-reasoned recommendations to executive leadership.


• Use Dynatrace’s observability platform as a strategic advantage to monitor, measure, and continuously improve the reliability, performance, and business impact of internally deployed AI solutions.

AI Governance and Responsible AI

• Mature and own Dynatrace’s enterprise AI governance framework, including acceptable use policies, risk tiering, human-in-the-loop thresholds, and decision authority standards for AI systems across the organization.


• Partner with Legal, Risk, Security, Compliance, and Works Council stakeholders to ensure AI deployments meet requirements for data privacy, regulation, security, and labor co-determination.


• Design AI risk assessment processes that enable responsible adoption at speed, creating guardrails that protect the organization without slowing practical innovation.


• Define data usage policies, model transparency expectations, and audit standards so Dynatrace can demonstrate responsible AI practices to regulators, customers, employees, and internal stakeholders.


• Serve as the senior internal voice on AI ethics, fairness, and accountability, building confidence in how AI-enabled decisions are made, reviewed, and governed. 

Organizational AI Capability and Maturity

• Design and execute an enterprise AI enablement program that includes executive briefings, AI literacy workshops, department-level playbooks, and training curricula to raise AI maturity at every level.


• Establish an AI Center of Excellence to standardize delivery practices, capture institutional knowledge, and scale proven AI patterns across departments and workflows.


• Define and track enterprise AI maturity metrics, measuring adoption, capability growth, and the organizational shift toward AI-augmented work.

Executive Engagement and Value Realization

• Serve as the primary AI thought leader and internal advisor to Dynatrace’s leadership, translating complex AI developments into clear strategic guidance and business cases.


• Own portfolio-level AI value realization by defining success metrics such as productivity gains, cycle-time reduction, cost savings, and manual work eliminated; build executive-facing ROI reporting and communicate impact on a regular cadence.


• Stay current on emerging AI technologies, vendors, and industry practices, maintaining a strong external perspective that informs Dynatrace’s internal strategy. 

What will help you succeed

Minimum Requirements 

• 12+ years of progressive experience in enterprise technology, AI/ML, or digital transformation leadership — with at least 3–5 years in a senior director or equivalent role with demonstrated portfolio ownership.

Preferred Requirements 

• Demonstrated success shaping and operationalizing enterprise AI strategies that drive measurable impact across global, cross-functional organizations.


• Deep knowledge of modern AI technologies including large language models (LLMs), agentic frameworks, retrieval-augmented generation (RAG), vector databases, and automation platforms — with the credibility to evaluate vendor claims and guide architectural decisions.


• Experience owning AI governance: building acceptable use policies, risk tiering frameworks, human oversight models, and working with Legal and Compliance on enterprise-wide guardrails.


• Demonstrated experience building and leading high-performing teams — including hiring, developing, and retaining AI product managers and technical program leads.


• Strong executive presence and communication skills: able to explain complex AI concepts to non-technical audiences, build business cases for AI investment, and present confidently to C-suite and board-level stakeholders.


• Experience building AI centers of excellence, capability programs, or organizational enablement initiatives that measurably increased AI maturity.


• Familiarity with enterprise platforms — ServiceNow, Salesforce, SAP, or similar — and an understanding of how AI capabilities are embedded within existing business systems and workflows.


• Exposure to data platform architecture (Snowflake, medallion/lakehouse patterns, semantic layers) and how governed enterprise data enables AI at scale.


• Track record of leading enterprise transformation through influence — driving adoption, managing change, and building cross-functional alignment without direct authority over every stakeholder.


• Experience with build/buy/partner decisions at the portfolio level, including vendor evaluation, contract negotiation support, and post-implementation performance tracking.


• Bonus: hands-on experience with observability or monitoring platforms — Dynatrace or similar — applied to AI system performance and reliability. 

This is a remote eligible position out of Canada.  Candidates are required to work EST hours for this position. 

Why you will love being a Dynatracer

• Dynatrace is a leader in unified observability and security.


• We provide a culture of excellence with competitive compensation packages designed to recognize and reward performance.


• Our employees work with the largest cloud providers, including AWS, Microsoft, and Google Cloud, and other leading partners worldwide to create strategic alliances.


• You'll get to work at the forefront of innovation with Dynatrace Intelligence—the industry's first agentic operations system. Bringing together deterministic and agentic AI, it helps teams understand what's happening, why it matters, and what to do next— automatically.


• Over 50% of the Fortune 100 companies are current customers of Dynatrace.

Compensation and Rewards

DOE, salary $208K CAD - $260K CAD, plus Health, Dental, Life, STD, LTD, 401K, PTO. Total compensation may vary depending on candidate experience/education and location.