VP, Engineering

Vice President, Engineering: Cornerstone OnDemand | Executive Leadership | Remote-Flexible About Cornerstone: Cornerstone helps organizations unlock the potential of their people through technology, content, expertise and specialized focus. Its solutions span learning, talent management, performance, recruiting and workforce development, serving millions of users across thousands of organizations worldwide. Cornerstone is embarking on a transformative journey to build WorkforceOS, a next-generation, AI-native Human Capital Management (HCM) platform that unifies the employee lifecycle into a single, intelligent operating system for the modern workforce.

WorkforceOS will connect employee data, skills intelligence, learning, performance, talent and workforce capabilities to help organizations make smarter workforce decisions, develop their people and build the capabilities needed for the future. About the Opportunity: We are seeking a Vice President, Engineering to be a founding member of the WorkforceOS leadership team. This is an opportunity to define and build the technology foundation for a next-generation enterprise HCM platform.

You will own the end-to-end engineering strategy, technical vision, architecture and execution for WorkforceOS, building a scalable, secure, resilient and AI-native platform that can serve global enterprise customers. You will have end-to-end ownership of the WorkforceOS engineering organization and technology architecture, with the autonomy to make key technology decisions and establish the engineering practices needed to build and scale the platform. You will partner with Cornerstone's centralized platform teams and engineering organizations across business lines to leverage shared capabilities, drive interoperability and ensure alignment with enterprise technology standards.

A key aspect of this role will be balancing greenfield platform development with the modernization and reuse of existing Cornerstone technology and capabilities. You will also lead the technology strategy for transitioning customers from legacy HCM platforms to WorkforceOS, ensuring seamless migrations with minimal customer disruption, effort and business impact. You will build and lead a world-class global engineering organization spanning application engineering, platform engineering, AI/ML, data engineering, quality engineering, infrastructure and reliability engineering.

Working in close partnership with Product Management, Design, Data Science and the broader Cornerstone technology organization, you will translate product vision into an exceptional technology platform and customer experience. This role requires a strong technology leader who combines architectural depth, engineering excellence, operational discipline and the ability to build and scale high-performing engineering organizations. In this role you will... 1.

Technology Vision Architecture Define and own the technology vision, engineering strategy and end-to-end architectural direction for WorkforceOS. Architect and build a modern, cloud-native, API-first and AI-native enterprise HCM platform designed for global scale. Establish a modular, extensible and interoperable architecture that supports multiple HCM capabilities while enabling a unified employee and administrator experience.

Own architecture decisions across application services, platform services, data architecture, integration frameworks and shared capabilities. Establish platform foundations that enable rapid product innovation, extensibility, configuration and customization without compromising upgradeability or maintainability. Drive a balanced technology strategy that leverages and modernizes existing Cornerstone capabilities while introducing new technology and architectural foundations where needed.

Ensure seamless integration with Cornerstone's existing products, enterprise ecosystem and third-party platforms. Drive technology choices and architectural trade-offs that balance speed to market, scalability, cost efficiency, reliability and long-term maintainability. Establish architecture standards, design principles, technical governance and engineering best practices for WorkforceOS.

Partner with centralized platform engineering and architecture teams to leverage shared infrastructure and services, drive interoperability and align with enterprise-wide technology standards, while retaining end-to-end ownership of WorkforceOS architecture. 2. AI-Native Engineering Innovation Lead the engineering strategy for building AI-native capabilities into WorkforceOS. Establish the technical foundations for intelligent agents, AI-powered workflows, predictive intelligence, skills inference and personalized experiences.

Drive the integration of large language models, machine learning, retrieval-augmented generation and agentic AI capabilities into enterprise workflows. Build secure and scalable AI infrastructure, including model orchestration, evaluation frameworks, observability, governance and cost management. Establish standards for responsible AI, data privacy, security, explainability and human oversight.

Partner with Product Management and Data Science to identify and accelerate opportunities where AI can fundamentally simplify workflows and create differentiated customer value. Drive adoption of AI-assisted software engineering and modern developer tools to improve engineering productivity, quality and speed. Continuously evaluate emerging technologies and translate relevant innovations into competitive platform capabilities. 3.

Engineering Execution Delivery Excellence Own end-to-end engineering execution and delivery of the WorkforceOS product roadmap. Establish a high-performance engineering operating model that enables predictable delivery, rapid iteration and continuous innovation. Partner closely with Product Management to translate product strategy into executable technical plans, milestones and delivery commitments.

Drive engineering productivity through modern development practices, automation, developer platforms and AI-assisted software engineering. Establish strong engineering disciplines across architecture and design reviews, code quality, testing, continuous integration, continuous delivery and release management. Drive a culture of engineering ownership, accountability and continuous improvement.

Ensure engineering teams can deliver at speed without compromising quality, security or architectural integrity. Establish appropriate engineering metrics to measure delivery predictability, productivity, quality and customer impact. Continuously improve engineering effectiveness through automation, standardization, simplification and adoption of modern development practices. 4.

Platform Reliability, Security Operational Excellence Own the reliability, availability, scalability, performance and operational excellence of the WorkforceOS platform. Build a secure-by-design platform that meets the requirements of large, complex global enterprises. Establish robust practices for identity and access management, data protection, encryption, tenant isolation and regulatory compliance.

Drive observability, incident management, disaster recovery, business continuity and service-level objectives. Ensure the platform is designed for high availability, resilience and predictable performance across global markets. Establish effective DevSecOps, Site Reliability Engineering (SRE) and platform engineering capabilities.

Drive continuous improvement in cloud infrastructure efficiency, platform performance and total cost of ownership. Ensure enterprise-grade security, privacy and compliance requirements are addressed in partnership with Cornerstone's central security and compliance organizations. 5. Data Integration Architecture Define the data architecture and engineering foundations that enable a unified workforce data model across WorkforceOS.

Establish robust data ingestion, processing, storage and integration capabilities to support real-time and analytical workloads. Enable a consistent and extensible data foundation for employee records, organizational structures, skills intelligence, talent and workforce insights. Drive the development of enterprise APIs, event-driven architecture and integration frameworks.

Ensure seamless connectivity with HRIS, payroll, ERP, identity management and other enterprise systems. Enable secure data access and interoperability across Cornerstone products and third-party ecosystems. Partner with Product and Data Science to establish the data foundations needed for AI, analytics and intelligent decision-making.

Establish data governance, quality, lineage and lifecycle management practices that support enterprise-grade workforce data. 6. Customer Migration Platform Transformation Own the engineering strategy and technical execution for transitioning customers from Cornerstone's legacy HCM platforms to WorkforceOS. Design scalable, repeatable and highly automated migration frameworks that enable seamless customer transitions with minimal customer effort and business disruption.

Develop strategies for data migration, transformation, validation and reconciliation, ensuring data integrity, accuracy, security and continuity throughout the migration lifecycle. Establish migration tooling, automation, compatibility frameworks and processes that accelerate customer onboarding and reduce migration costs. Design phased migration, coexistence and cutover strategies that allow customers to transition at scale while maintaining business continuity.

Ensure continuity of critical customer workflows, integrations, configurations, historical data and user experiences during migration. Build robust validation, monitoring, rollback and recovery mechanisms to minimize migration risks and ensure customer confidence. Partner with Product Management, Customer Success, Professional Services and other customer-facing teams to define migration approaches that minimize customer involvement and accelerate time to value.

Establish migration success metrics, including migration velocity, automation levels, data accuracy, customer effort, disruption and time to completion. Drive continuous improvements in migration efficiency and scalability, enabling the business to transition its installed customer base to WorkforceOS at scale. 7. Engineering Organization Leadership Build, lead and develop a high-performing global engineering organization from the ground up, with end-to-end ownership across application engineering, platform engineering, AI/ML, data engineering, quality engineering, infrastructure and SRE.

Recruit, develop and retain exceptional engineering leaders, architects and engineers across multiple technology disciplines. Establish the engineering organizational structure, technical leadership model and operating cadence needed to support WorkforceOS. Build a strong culture of engineering excellence, ownership, innovation, collaboration and accountability.

Develop strong technical leadership and career progression frameworks, creating opportunities for engineers to grow and take on increasing responsibility. Establish clear engineering ownership across platform, product domains, infrastructure, data and AI capabilities. Drive a culture of continuous learning, technical experimentation and adoption of modern engineering practices.

Build an inclusive and globally distributed engineering organization that can scale with the business. Develop an engineering talent strategy that attracts exceptional talent and creates a high-performance environment. 8. Cross-Functional Executive Partnership Work closely with the GM of WorkforceOS to translate business strategy and product vision into technology strategy, investment priorities and execution plans.

Partner closely with the VP of Product Management to jointly drive product delivery, roadmap execution, technical feasibility and customer outcomes. Establish strong partnerships with engineering and technology leaders across Cornerstone's business lines to drive architectural alignment, platform integration, technology reuse and ecosystem interoperability. Collaborate with GMs and product leaders across business lines to identify opportunities for shared technology investments, integration and innovation.

Work closely with Cornerstone's CTO, CPO and broader technology leadership to align WorkforceOS with the company's technology strategy, architectural standards and long-term platform vision. Partner with centralized platform teams to leverage common infrastructure, services and capabilities while maintaining clear ownership and accountability for WorkforceOS engineering outcomes. Drive effective engineering operating cadences, technical reviews, delivery governance and executive communication.

Partner with Sales, Customer Success and strategic customers to address technical requirements, enterprise architecture considerations and complex customer engagements. Represent WorkforceOS in executive forums, customer engagements and strategic technology discussions. You've got what it takes if you have: 18+ years of experience in software engineering and technology leadership, with significant experience building enterprise-scale software platforms. 8+ years of experience leading large engineering organizations, including managing senior engineering leaders.

Proven experience building and scaling complex, multi-tenant enterprise SaaS platforms. Strong architectural expertise across cloud-native systems, distributed computing, microservices, APIs, event-driven architecture and enterprise integration. Demonstrated ability to design and deliver highly available, secure and scalable enterprise software.

Experience building AI-enabled platforms or integrating AI, machine learning and generative AI capabilities into enterprise products. Strong understanding of data architecture, analytics platforms, data engineering and enterprise data governance. Experience establishing and scaling engineering organizations, technical leadership structures and engineering operating models.

Proven track record of delivering complex, multi-year technology programs with strong execution discipline. Experience with cloud platforms, DevSecOps, SRE, CI/CD and modern software engineering practices. Experience with large-scale enterprise platform modernization, customer migrations or technology transformations is highly desirable.

Demonstrated ability to work across organizational boundaries and influence technology decisions in complex, global engineering environments. Excellent communication, strategic thinking and executive stakeholder management skills. Experience leading globally distributed engineering teams.

Leadership Attributes: Technology Visionary: Able to define the technology foundation for a next-generation enterprise platform and make sound long-term architectural decisions. Engineering Craftsman: Sets high standards for architecture, software quality, engineering practices and operational excellence. AI-First Technologist: Understands how AI will transform software development, enterprise platforms and business workflows.

Execution Focused: Converts ambitious technology strategies into predictable, high-quality delivery. Platform Thinker: Balances individual product requirements with reusable platform capabilities, extensibility and long term scalability. Customer Focused: Understands the importance of customer experience during platform transformation and prioritizes seamless migrations with minimal disruption.

Transformation Leader: Has experience modernizing legacy platforms and executing complex technology transformations while maintaining business continuity. Organizational Builder: Has demonstrated the ability to build strong engineering organizations and develop exceptional technical leaders. Business Oriented: Understands the connection between engineering investments, product differentiation, customer outcomes and business growth.

Collaborative Leader: Builds strong partnerships with Product, Design, Data Science and the broader technology organization. The Opportunity: This is a unique opportunity to architect and build the technology foundation of a category-defining, AI-native HCM platform. You will shape the engineering organization, platform architecture and technical culture that will power the future of WorkforceOS, while leading the transformation of Cornerstone's HCM technology and customer base onto this next-generation platform. #LI-Onsite