[Remote] Sr. Principal Program Manager - AI Transformation

Note: The job is a remote job and is open to candidates in USA. G-P is a leading SaaS-based Global Employment Platform that enables clients to expand into over 180 countries efficiently. They are seeking a Sr. Principal Program Manager to oversee AI transformation initiatives, ensuring alignment between business areas and enterprise technology teams while managing a multi-year roadmap for Finance, HRIS, and Legal transformations.

Responsibilities

• Lead the collaboration between the business areas and aligned enterprise tech team to ensure alignment between changing ways of working and tech/AI enabled automation and agentic solutions
• Collaborate with functional leaders and enterprise tech team on the roadmap and measurement of impact/benefits, adoption and enablement
• Navigate complex cross-functional dependencies to keep the engine moving—holding engineering, enterprise applications, and business teams accountable for hitting milestones and delivering measurable ROI on agentic initiatives
• Portfolio Governance & Roadmap Orchestration: Establish the standards for project intake, prioritization, and status reporting for the Finance, HRIS, and Legal infrastructure. Manage the "Golden Path" of initiatives that optimize the workflow journey
• AI Program Lifecycle: Oversee the programmatic rollout of AI-forward capabilities (e.g., automated legal review, automated financial workflows). Manage the pilot-to-production lifecycle and measurable business impact
• Dependency & Risk Mitigation: Proactively identify and manage critical path dependencies between Finance, HRIS, and Legal engines and the backend financial/contracting systems. Mediate resource contention across matrixed engineering and design teams
• Executive Steering & Communication: Chair high-level steering committees (SVP/C-Suite) to provide data-driven insights into portfolio health, budget variance, and risk-adjusted delivery timelines

Skills

• 15+ Years in Program Management
• Proven track record of managing $20M+ portfolios within a global enterprise SaaS environment
• Matrixed Leadership: Expert experience working across Enterprise Application Engineering and Finance/Legal teams to deliver unified business solutions
• Methodology Mastery: Advanced proficiency in PMP/PgMP frameworks, focusing on Risk Management, Resource Leveling, and Value Realization
• Domain Experience: Must-have experience within HRIS and Legal environments
• Location: Candidates can be in any US time zone (limited to the US, but open to strong candidates from Latin America)
• Experience with Workday ERP, Workday HRIS, and Workday Adaptive
• Experience with DocuSign
• Experience with incentive/compensation systems, specifically CaptivateIQ

Benefits

• Competitive compensation and benefits
• Eligible for additional compensation as follows: Sales Roles: This position is eligible for a commission structure in addition to base salary.
• Non-Sales Roles: This position is eligible for an annual bonus which is paid dependent on various factors, including and without limitation, individual and company performance in addition to base salary.
• Generous paid parental leave
• Flexible time off
• Spending accounts
• Medical insurance
• Dental insurance
• Vision insurance
• Sabbatical after 5 years

Company Overview