Sr. Principal Program Manager - AI Transformation

G-P

12h•$176,000 - $221,000•Remote

About The Position

As a Sr. Principal Program Manager, you will be the connective tissue between the functional business areas, their AI transformation, and the enterprise tech teams developing automation and agentic solutions. This role is about architecting the shift from traditional roles to tech-enabled automation and agentic AI workflows that redefine how our teams work. This role is responsible for the rigorous management of a multi-year roadmap that integrates corporate initiatives with a global Finance, HRIS, and Legal transformation. You will serve as the primary operational link between Finance, HRIS, and Legal business stakeholders. You will ensure that high-stakes workstreams are delivered on time, within budget, and aligned with corporate ROI targets, while maintaining a focus on a seamless, AI-augmented operational flow.

Requirements

15+ Years in Program Management
Proven track record of managing $20M+ portfolios within a global enterprise SaaS environment.
Expert experience working across Enterprise Application Engineering and Finance/Legal teams to deliver unified business solutions.
Advanced proficiency in PMP/PgMP frameworks, focusing on Risk Management, Resource Leveling, and Value Realization.
Must-have experience within HRIS and Legal environments.
Candidates can be in any US time zone (limited to the US, but open to strong candidates from Latin America).

Nice To Haves

Experience with Workday ERP, Workday HRIS, and Workday Adaptive.
Experience with DocuSign.
Experience with incentive/compensation systems, specifically CaptivateIQ.

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.
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.
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.
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.
Chair high-level steering committees (SVP/C-Suite) to provide data-driven insights into portfolio health, budget variance, and risk-adjusted delivery timelines.