Director, AI Engineering

• Lead and oversee multiple engineering teams across the full software development lifecycle — from requirements and architecture through implementation, testing, deployment, and operations.
• Define and drive technical vision and architecture strategy, ensuring systems are scalable, resilient, and aligned with long-term organizational goals.
• Own end-to-end delivery across portfolios/programs, ensuring alignment with business priorities, timelines, and quality expectations.
• Establish and standardize engineering best practices across teams, including design reviews, code quality standards, testing strategies, and CI/CD adoption.
• Drive consistency and excellence in software development processes, system reliability, and engineering productivity.
• Partner closely with Product, UX, QA, and other stakeholders to ensure effective planning, prioritization, and execution of roadmaps.
• Oversee proactive management of technical debt, system performance, and operational reliability at scale.
• Ensure effective incident management frameworks, root cause analysis, and continuous improvement for system uptime and performance.
  
  

• Lead, mentor, and grow engineering managers and senior technical leaders, building a scalable organizational structure.
• Drive hiring strategy to attract and retain top engineering talent across levels.
• Establish clear career frameworks, succession planning, and leadership development initiatives.
• Foster a culture of accountability, innovation, inclusion, and continuous learning across the organization.
• Provide ongoing coaching, performance management, and feedback to leaders and their teams.
• Oversee resource planning, organizational design, and capacity management to align with strategic priorities.
  
  

• Partner with executive leadership to define and execute long-term technology and engineering strategy.
• Drive engineering roadmaps aligned with product vision and business objectives.
• Provide regular executive-level updates, including progress, risks, and investment trade-offs.
• Evaluate and adopt emerging technologies, tools, and platforms to enhance innovation and efficiency.
• Lead organizational improvements across Agile practices, delivery frameworks, and operational processes.
• Collaborate with DevOps, Infrastructure, Security, and Data teams to ensure operational excellence, scalability, and compliance.
• Represent engineering in executive forums, cross-functional planning, and architectural governance discussions.
  
  

• Bachelor’s or Master’s degree in Computer Science, Software Engineering, or a related field, or equivalent practical experience.
• 15+ years of software engineering experience, with 5+ years in engineering leadership roles managing managers or multiple teams.
• Proven track record of leading large-scale, complex software programs and distributed engineering organizations.
  
  

• Strong background in software engineering, system design, and distributed systems architecture.
• Hands-on experience in technologies such as Java, C#, Python, JavaScript/TypeScript, or Go (prior coding experience expected, even if not day-to-day).
• Deep expertise in cloud platforms, microservices architecture, and API design patterns.
• Strong knowledge of data systems (SQL/NoSQL), caching, and large-scale data architecture.
• Experience with CI/CD, DevOps practices, containerization (Docker/Kubernetes), and infrastructure-as-code.
• Solid understanding of security, scalability, performance engineering, and reliability best practices.
  
  

• Exceptional leadership and communication skills, with the ability to influence at all levels, including executive stakeholders.
• Strong strategic thinking and decision-making capabilities with a focus on business impact and outcomes.
• Demonstrated success in building and leading high-performing, geographically distributed teams.
• Ability to manage complex priorities, ambiguity, and large-scale organizational challenges.
• Strong collaboration skills with the ability to align cross-functional teams toward common goals.
• High sense of ownership, accountability, and commitment to delivery excellence.
  
  

• Experience in SaaS or enterprise product organizations at scale.
• Exposure to AI/ML platforms and integrating AI capabilities into products.
• Experience leading platform modernization, cloud transformation, or large-scale migrations.
• Familiarity with talent management, HR tech, or learning management systems.
  
  

In 1999, Cornerstone started with a simple (but bold) idea — to improve access to education on a global basis through online learning.

Cornerstone has come a long way since then, but our heritage of focusing on the importance of helping people learn and grow at work remains the same.

Today, we're a diverse team of talent experts — AKA Cornerstars — who understand big ideas, solve problems, and focus on innovating new solutions that deliver great experiences for our customers and their people. Together, we are obsessed with helping our customers meet the future, ready.