Principal Program Manager

• 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.
  
  

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.