Sr. Principal Program Manager - AI Transformation

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.

What You’ll Do

• 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.

Do you have experience in SaaS platforms?, * 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).

Preferred Requirements:

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

3.53.5 out of 5 stars Boston, MA Remote $176,000 - $221,000 a year - Full-time, Pulled from the full job description

• Paid parental leave
• Parental leave
• Health insurance
• Vision insurance
• Dental insurance
• Sabbatical, The annual gross base salary range for this position is $176,000 - $221,000 plus variable compensation.

We will consider for employment all qualified applicants, including those with arrest records, conviction records, or other criminal histories, in a manner consistent with the requirements of any applicable state and local laws, including the City of Los Angeles’ Fair Chance Initiative for Hiring Ordinance, the San Francisco Fair Chance Ordinance, and the New York City Fair Chance Act.

Actual compensation for this position may vary and will depend on multiple factors such as relevant qualifications, experience, education, and geographic location. For Full-Time Regular Employees, this position is also 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., G-P values its employees and offers excellent benefits and perks including generous paid parental leave, flexible time off, spending accounts, medical insurance, dental insurance, vision insurance, sabbatical after 5 years and more.

Our leading SaaS-based Global Employment Platform enables clients to expand into over 180 countries quickly and efficiently, without the complexities of establishing local entities. At G-P, we’re dedicated to breaking down barriers to global business and creating opportunities for everyone, everywhere.

Our diverse, remote-first teams are essential to our success. We empower our Dream Team members with flexibility and resources, fostering an environment where innovation thrives and every contribution is valued and celebrated.

The work you do here will positively impact lives around the world. We stand by our promise: Opportunity Made Possible. In addition to competitive compensation and benefits, we invite you to join us in expanding your skills and helping to reshape the future of work.

At G-P, we assist organizations in building exceptional global teams in days, not months-streamlining the hiring, onboarding, and management process to unlock growth potential for all.