Principal Program Manager

Principal Program Manager

Cornerstone OnDemand is looking for a Principal Program Manager who will drive the planning, execution, and delivery of complex, cross-functional technical programs. You will work at the intersection of engineering, product, and business teams to ensure large-scale initiatives are delivered with clarity, predictability, and impact. This role requires a strong technical foundation combined with exceptional program management skills to orchestrate multiple workstreams and stakeholders toward shared outcomes.

In this role, you will...

Program Planning & Execution:

• Own end-to-end program management for large-scale, cross-functional technical initiatives spanning multiple engineering teams, products, and business units.
• Define program scope, milestones, deliverables, success criteria, and resource requirements in collaboration with engineering and product leadership.
• Build and maintain detailed program plans, roadmaps, and schedules with clear dependencies, critical paths, and risk mitigation strategies.
• Drive program execution through structured governance - standups, status reviews, steering committee meetings, and escalation workflows.
• Track and report program health, progress, risks, and blockers to senior leadership and stakeholders through dashboards and executive summaries.
• Manage program-level trade-offs across scope, timeline, quality, and resources - making recommendations grounded in data and technical context.
• Conduct retrospectives and post-mortems to capture lessons learned and drive continuous improvement in delivery processes.
• Identify process bottlenecks and inefficiencies across teams and implement improvements to accelerate delivery cycles.

• Partner with engineering leaders and architects to understand system designs, technical dependencies, and integration points across programs.
• Facilitate architecture and design reviews to ensure alignment across teams and identify cross-cutting concerns early.
• Coordinate platform migrations, infrastructure upgrades, API versioning, and other technical initiatives that span multiple teams.
• Partner with DevOps and SRE teams to ensure release readiness, deployment coordination, and operational handoffs for program deliverables.
• Define and drive Agile-at-scale practices (SAFe, Scrum of Scrums, or similar) across engineering teams to improve delivery predictability and velocity.
• Facilitate alignment between product roadmaps, engineering capacity, and business priorities to ensure realistic commitments.

• Serve as the central point of communication for program status, decisions, and escalations across engineering, product, design, QA, and business teams.
• Translate complex technical concepts and program details into clear, concise updates for executive leadership and non-technical stakeholders.
• Manage stakeholder expectations proactively - surfacing trade-offs, timeline impacts, and scope changes early with data-backed recommendations.
• Build and maintain a risk management framework - proactively identifying, assessing, and mitigating risks before they become blockers.
• Manage cross-team dependency tracking, capacity planning, and sprint/release coordination.
• Build strong relationships across the organization to enable effective collaboration and influence without authority.

• Bachelor's or Master's degree in Computer Science, Software Engineering, Information Technology, or a related field, or equivalent practical experience.
• 10+ years of experience in technical program management, engineering project management, or a related role within software product organizations.
• 5+ years of hands-on software engineering or technical lead experience (prior to or alongside program management).
• Proven track record of successfully delivering large-scale, cross-functional technical programs on time and within scope.

• Strong understanding of software development lifecycle, system architecture, distributed systems, and cloud platforms (Azure preferred).
• Familiarity with microservices architecture, API design, CI/CD pipelines, and modern DevOps practices.
• Ability to read and understand code, technical design documents, and architecture diagrams at a level sufficient to assess risks and dependencies.
• Experience with Agile/Scrum methodologies and scaling frameworks.
• Proficiency with program management and collaboration tools such as Jira, Azure DevOps, Confluence, Smartsheet, or MS Project.

• Excellent written and verbal communication skills with the ability to tailor messaging for technical and executive audiences.
• Strong facilitation skills - able to lead productive meetings, drive decisions, and resolve conflicts constructively.
• Exceptional organizational skills with the ability to manage multiple complex programs simultaneously.
• Proven ability to build trust and influence across engineering, product, and business functions.
• Proactive and self-driven with a strong sense of ownership over program outcomes.

• Experience in SaaS/enterprise product development environments.
• Exposure to AI/ML programs and their unique delivery challenges.
• Familiarity with talent management, HR tech, or learning management domains.