Note: The job is a remote job and is open to candidates in USA. Cypress HCM is seeking an experienced Program Manager to lead high-impact People Technology initiatives and transformations. The role partners with People business leaders and technology delivery teams to manage program strategy, governance, cross-functional execution, enterprise technology lifecycles, risks, budgets, and operational improvements.
Responsibilities
- Lead end-to-end program delivery for complex, multi-year initiatives people technology transformations (Workday, Greenhouse, Jira, Zendesk, Confluence)
- Execute strategic planning sessions and cross-functional prioritization with Corporate Engineering, IT, Privacy and Security leadership teams to align program roadmaps with business objectives
- Manage program governance through biweekly and monthly strategic initiative reviews, risk assessments, and executive reporting that drives accountability and informed decision-making
- Orchestrate cross-functional program teams spanning engineering, IT operations, security, privacy, compliance, and People stakeholders to ensure seamless program delivery
- Drive enterprise technology lifecycle management including vendor selection, contract negotiations, system integrations, and sunset/migration planning
- Execute operational excellence initiatives such as infrastructure optimization, business process automation, disaster recovery planning, and performance monitoring implementations
- Proactively manage program risks and dependencies, implementing course corrections and stakeholder communications to keep initiatives on track
- Partner with fi nance and strategy teams to manage program budgets, track ROI, and optimize resource allocation across the technology portfolio
Skills
- 8+ years executing complex transformation programs in operations consulting, strategy, or enterprise technology
- 6+ years leading enterprise technology program delivery including HCM platforms (Workday, Greenhouse)
- Proven track record executing full-cycle transformations from business case development through implementation, change management, and operational handoff
- Experience leading privacy and security programs such as GDPR/CCPA compliance, security framework implementations, identity management systems, or data governance initiatives
- Strong executive communication skills with ability to manage up to C-level stakeholders and translate complex technical and regulatory requirements into business impact
- Demonstrated experience managing technology vendors, complex procurement processes, and success managing technology budgets exceeding $1M annually
- Track record coordinating cross-functional teams across IT, Engineering, Security, Privacy, Compliance, Finance, HR, and business operations
- Strong business acumen with the ability to identify strategic needs, lead all aspects of planning with sound business recommendations, and generate alignment with key business partners
- Forward-thinking strategist with proven success in translating strategy to tactical plans with high-quality execution and delivery
- Champion AI and automation initiatives across the enterprise, identifying opportunities to leverage generative AI for process optimization and implementing solutions and a commitment to continuous improvement and pursuit of excellence
- An empathetic leader style and a strong sense of self-awareness
Company Overview