Senior Director, AI Engineering

Sr Director of Engineering, AI & Machine Learning:

About Cornerstone:

Cornerstone provides an AI-powered Talent Experience Platform for unified content discovery, knowledge management, and personalized learning experiences across the career journey. Our award-winning platform is used globally by Fortune 500 companies and government organizations to solve complex discovery, curation, and recommendation challenges across internal, external, and tacit knowledge sources.

As part of a significant investment in a new AI product, Cornerstone is building next-generation AI capabilities that will expand and enhance how customers learn, grow, and perform. We are seeking a Sr Director of Engineering, AI & Machine Learning to lead the technical execution and team delivery for this strategic initiative.

The Role:

This role blends engineering leadership, platform ownership, and people management within an AI-focused product. You will lead a team of Software, Machine Learning Engineers, and Managers responsible for building, deploying, and operating AI-driven capabilities including recommendation systems, generative AI, and data-driven insights.
You will partner closely with Product, Data Science, Platform, and Client-facing teams to ensure AI solutions are scalable, secure, and production-ready from day one.

In this role you will..

Technical & Platform Leadership

• Lead the design, development, and delivery of AI-driven features for a new AI product, including recommendation systems, generative AI, and data visualization.
• Partner with Product and domain teams to shape future designs and ensure solutions are feasible, scalable, automated, secure, and operationally supportable.
• Define platform architecture decisions, including CI/CD pipelines, cloud deployment strategies, and automation supporting the ML lifecycle.
• Partner with ML specialists to establish best practices for MLOps, including model deployment, monitoring, retraining, and production reliability.
• Drive experimentation and rapid iteration to improve model performance, engagement, and real-world impact.

Execution & Delivery

• Own execution and delivery across AI/ML initiatives, ensuring alignment with product roadmaps and business priorities.
• Collaborate with engineering leaders to ensure predictable, high-quality delivery.
• Define and track metrics for system reliability, customer impact, and product success.
• Engage with customers as needed for technical discussions, escalations, and AI-driven enhancements.

People & Organizational Leadership

• Build, lead, and develop a team of Software and ML engineers in a highly autonomous environment.
• Set clear technical direction while empowering teams to operate independently.
• Coach engineers and managers on technical depth, operational discipline, and delivery excellence.
• Partner with recruiting and leadership to scale the team as the product and investment grow.

Technology Stack & Capabilities

• Programming & Data: Python, Java/Kotlin and related data and visualization libraries.
• Backend & Data Systems: RESTful APIs, distributed systems, analytical databases.
• AI / ML Frameworks: PyTorch, TensorFlow, Hugging Face, OpenAI APIs.
• ML Pipelines & MLOps: Apache Airflow, Kubeflow, Ray (or equivalent).
• Cloud & DevOps: CI/CD pipelines, cloud deployment, monitoring, and infrastructure automation.
• Development Practices: Agile / Lean methodologies.

Who You Are:

• A hands-on technical leader who can go deep when needed but primarily operates at the system, platform, and team level.
• Comfortable making independent decisions in fast-moving, ambiguous environments.
• A strong collaborator and communicator across technical and non-technical audiences.
• Delivery-focused with a track record of shipping complex products on time.
• Deeply customer-focused with a passion for AI innovation and continuous improvement.

You’ve got what it takes if you…

• Bachelor’s or Master’s degree in Computer Science or a related field, or equivalent experience.
• 15+ years of experience designing and building scalable, resilient systems.
• 9+ years leading engineering teams and initiatives in enterprise or Tier 1 companies.
• Experience delivering AI-integrated products, with working knowledge of ML concepts, LLMs, and generative AI.
• Demonstrated ability to quickly learn and apply new technical domains.
• Solid experience with system availability, security, performance, and operational excellence.
• Excellent communication and presentation skills, including the ability to explain complex technical concepts to non-technical stakeholders.
• A strong customer-service mindset and commitment to high-quality delivery.

#LI-Onsite

Our Culture:

Spark Greatness. Shatter Boundaries. Share Success. Are you ready? Because here, right now – is where the future of work is happening. Where curious disruptors and change innovators like you are helping communities and customers enable everyone – anywhere – to learn, grow and advance. To be better tomorrow than they are today.

Who We Are:

Cornerstone powers the potential of organizations and their people to thrive in a changing world. Cornerstone Galaxy, the complete AI-powered workforce agility platform, meets organizations where they are. With Galaxy, organizations can identify skills gaps and development opportunities, retain and engage top talent, and provide multimodal learning experiences to meet the diverse needs of the modern workforce. More than 7,000 organizations and 100 million+ users in 180+ countries and in nearly 50 languages use Cornerstone Galaxy to build high-performing, future-ready organizations and people today.

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