Senior Director, AI Engineering

We're looking for a Senior Director, AI Engineering This role is Remote

Cornerstone provides an AI-powered Talent Experience Platform enabling unified content discovery, knowledge management, and personalized learning experiences across the career journey. Our platform is trusted globally by leading enterprises and government organizations to address complex challenges in discovery, curation, and recommendation across diverse knowledge sources.

As we accelerate investment in transformative AI product initiatives, Cornerstone seeks a Senior Director of AI Engineering to architect, lead, and scale our next-generation AI capabilities. This strategic leader will drive the development and delivery of innovative AI solutions that redefine how millions of users learn, grow, and perform.

The Role

The Senior Director, AI Engineering, will own end-to-end technical strategy, execution, and organizational leadership for our AI engineering division. In collaboration with Product, Data Science, and Engineering leadership, you will help define and realize our AI vision—overseeing multiple teams responsible for AI-driven features, recommendation systems, generative AI, and actionable insights. You will set standards, ensure operational excellence, drive cross-functional adoption, and build a world-class engineering culture.

Responsibilities

Strategic & Technical Leadership

* Set and execute the strategic technical direction for AI engineering across all product lines, ensuring alignment with business objectives and product vision.

* Architect foundational AI platform components—recommendation systems, generative AI, ML infrastructure, and data analytics—to support scalability, security, and extensibility.

* Lead adoption of advanced machine learning methodologies, MLOps best practices, and production-grade AI reliability.

* Oversee platform-wide architecture decisions, including CI/CD pipelines, cloud-native deployments, and automation supporting the full ML lifecycle.

* Champion rapid experimentation and data-driven iteration, driving continuous improvement in model performance, user engagement, and measurable outcomes.

Execution & Delivery Excellence

* Own the execution and delivery of AI/ML initiatives across multiple engineering teams and products, ensuring quality, predictability, and impact.

* Define and monitor key metrics for system reliability, customer value, and product success.

* Partner with Product, Data Science, and Customer teams to ensure AI solutions meet operational, compliance, and stakeholder requirements.

* Serve as the technical spokesperson for AI initiatives, interfacing with executive leadership, clients, and external partners.

People & Organizational Leadership

* Build, mentor, and scale high-performing teams of engineering managers, software engineers, and ML specialists in a diverse, autonomous environment.

* Foster an inclusive culture of innovation, collaboration, and operational excellence.

* Develop organizational capabilities for talent acquisition, development, and retention as the AI portfolio evolves.

* Lead organizational change, championing Agile and Lean methodologies and driving cross-functional alignment.

Technology Stack & Capabilities

* Programming & Data: Python, Java/Kotlin, advanced data and visualization libraries.

* Backend & Data: RESTful APIs, distributed systems, analytical databases.

* AI/ML: PyTorch, TensorFlow, Hugging Face, OpenAI APIs.

* ML Pipelines & MLOps: Apache Airflow, Kubeflow, Ray (or equivalent).

* Cloud & DevOps: CI/CD, cloud deployment, monitoring, infrastructure automation.

* Development Practices: Scaled Agile/Lean, enterprise software development.

Qualifications

* Bachelor’s or Master’s degree in Computer Science or related field; PhD preferred.

* 15+ years of progressive experience designing and building scalable, mission-critical systems at enterprise scale.

* 10+ years of experience driving AI/ML strategy and delivery, including NLP, generative AI, and advanced recommendation systems.

* 8+ years in engineering leadership roles, including direct management of managers and multi-team organizations in high-growth environments.

* Deep expertise in ML algorithms (classical and deep learning), frameworks, system architecture, and operational best practices.

* Proven track record with high-availability architectures, security, performance, and compliance in cloud environments.

* Exceptional communication, executive presence, and stakeholder management skills.

* Deep commitment to customer-centric innovation and product excellence.

Total Rewards

At Cornerstone, our transparent total rewards program is based on three core tenets: equitable pay, market dynamic research, and skill-based appraisal.

The base salary range for this position is: $250000 - $400000 USD

In addition to competitive base pay, the compensation package for this role may include other incentives like bonus or commission, along with a generous benefits package. Additional base pay may be available if you reside in a high-cost metro area (New York City or San Francisco Bay Area).

This range reflects the minimum and maximum salary for this position. Where an individual’s pay falls within the range is determined by factors including, but not limited to, job-related skills, experience, and relevant education or training.

Our Culture

Our mission is to empower people, businesses and communities. A culture created less by what we do and more by who we are. When people ask what our team is about, we point to our core values: champion customer success, bring our best, achieve together, get stuff done, and innovate every day. We're always on the lookout for new, curious and capable people who can help us achieve our goal and we are seeking diversity in the people who join our team. We want to make sure that our company reflects the demographic of our customers, clients, and the communities in which we operate. So if you want to work for a friendly, global, inclusive and innovative company, we'd love to meet you!

What We Do

Cornerstone is a premier people development company. We believe people can achieve anything when they have the right development and growth opportunities. We offer organizations the technology, content, expertise and specialized focus to help them realize the potential of their people. Featuring comprehensive recruiting, personalized learning, modern training content, development-driven performance management and holistic employee data management and insights, Cornerstone’s people development solutions are successfully used by more than 100 million+ people in 180+ countries and in nearly 50 languages.

Cornerstone takes special care to ensure the security and privacy of the data of its users.

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Equal Employment Opportunity has been, and will continue to be, a fundamental commitment at Cornerstone OnDemand. All qualified applicants are given consideration regardless of race, religion, color, gender, sex, age, sexual orientation, gender identity, national origin, marital status, citizenship status, disability, veteran status, or any other protected class as provided in applicable Federal, State, or Local fair employment laws. If you have a disability or special need that requires accommodation, please contact us at [email protected] .