Senior Director, AI Engineering
Sr Director of Engineering, AI & Machine Learning:
About Cornerstone:
Cornerstone provides an AI-powered Talent Experience Platform for unifiedcontent discovery, knowledge management, and personalized learning experiencesacross the career journey. Our award-winning platform is used globally byFortune 500 companies and government organizations to solve complex discovery,curation, and recommendation challenges across internal, external, and tacitknowledge sources.
As part of a significant investment in a new AI product,Cornerstone is building next-generation AI capabilities that will expand andenhance how customers learn, grow, and perform. We are seeking a Sr Directorof Engineering, AI & Machine Learning to lead the technical executionand team delivery for this strategic initiative.
The Role:
This role blends engineering leadership, platform ownership, andpeople management within an AI-focused product. You will lead a teamof Software, Machine Learning Engineers, and Managers responsible for building,deploying, and operating AI-driven capabilities including recommendationsystems, generative AI, and data-driven insights.
You will partner closely with Product, Data Science, Platform, andClient-facing teams to ensure AI solutions are scalable, secure, andproduction-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.
- Partnerwith recruiting and leadership to scale the team as the product and investmentgrow.
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
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Perks and Benefits
Health and Wellness
- Health Insurance
- Health Reimbursement Account
- Dental Insurance
- Vision Insurance
- Life Insurance
- Short-Term Disability
- Long-Term Disability
- FSA
- HSA
- HSA With Employer Contribution
- Pet Insurance
- Mental Health Benefits
Parental Benefits
- Birth Parent or Maternity Leave
- Non-Birth Parent or Paternity Leave
- Fertility Benefits
- Family Support Resources
- Adoption Leave
Work Flexibility
- Flexible Work Hours
- Remote Work Opportunities
- Hybrid Work Opportunities
Office Life and Perks
- Casual Dress
- Snacks
- Company Outings
- On-Site Cafeteria
- Holiday Events
Vacation and Time Off
- Paid Vacation
- Unlimited Paid Time Off
- Paid Holidays
- Personal/Sick Days
- Leave of Absence
- Summer Fridays
Financial and Retirement
- 401(K) With Company Matching
- Stock Purchase Program
- Performance Bonus
- Relocation Assistance
- Financial Counseling
- Profit Sharing
Professional Development
- Tuition Reimbursement
- Promote From Within
- Work Visa Sponsorship
- Leadership Training Program
- Internship Program
- Shadowing Opportunities
- Access to Online Courses
Diversity and Inclusion
- Employee Resource Groups (ERG)
- Unconscious Bias Training
- Diversity, Equity, and Inclusion Program