Project Manager, Global Expansion

Overview

The Total Rewards Strategy & Enablement (TR S&E) team translates people strategy into business impact, building the infrastructure, programs, and systems that make Total Rewards work at scale. We're a small, high-leverage team that bridges strategy and execution, partnering with People leadership and cross-functional teams across Finance, Legal, and the business to turn ambiguous problems into durable programs.

Responsibilities

• Own end-to-end project management for entity employment readiness, including intake and scoping, requirements gathering, readiness gates, cross-functional approvals, and go-live and post-go-live handoff to People, Legal, and Finance functions
• Lead communications and change management across every entity lifecycle event, from kick-off briefings for executive sponsors and functional leads through employee-facing notifications before system cutover, ensuring every impacted audience has the right information at the right time
• Lead entity-related workstreams in mergers and acquisitions (M&A) integrations, advising on retain/merge/wind-down decisions, managing employer-of-record to entity transitions, and ensuring entity timelines are reflected in broader deal plans
• Serve as the primary coordination point across People functions (Total Rewards, People Systems, People Operations) and cross-functional leads (Payroll, Tax, Legal, Finance & Strategy, Treasury), aligning workstreams, driving decisions, and holding accountability against program timelines
• Partner with cross-functional stakeholders to anticipate and manage the full implications of entity lifecycle events before they create downstream risk; proactively surface dependencies, resolve blockers, and escalate where needed
• Build and continuously improve the infrastructure that makes entity management and employment readiness scalable: intake forms, project plan templates, handoff checklists, standard operating procedures (SOPs) and playbooks for common jurisdictions, compliance trackers, and retrospective documentation that feeds back into process improvements after each go-live
• Serve as the connective tissue across functional owners, surfacing cross-entity patterns, systemic risks, and program coverage gaps; support People leadership with structured analysis and reporting on portfolio health and entity-specific program decisions

Requirements

• 7+ years of program / operations management experience, including at least 3 years driving multi-stakeholder, cross-functional programs end to end
• Demonstrated experience in at least one of: Total Rewards (benefits, compensation, equity, talent mobility), Mergers & Acquisitions, People or Legal Operations, or People transformation programs at a global company
• A strong track record of taking ambiguous, multi-jurisdictional problems and converting them into structured, repeatable programs — ideally in a scaling environment where you built from 0 to 1
• Excellent written communication: you can produce a 1-page exec update, a stakeholder-tailored decision memo, and a step-by-step operator playbook with equal fluency
• Strong stakeholder management across senior cross-functional partners (Legal, Tax, Finance, People Systems); you know when to push, when to align, and when to escalate
• Comfort with data and systems — Workday and equity platforms (e.g., Shareworks/Carta) a plus; ability to spec requirements with People Systems
• A users-first mindset: you obsess over the Stripe employee experience and the operator experience, not just the program artifacts
• Familiarity with financial regulatory or licensing frameworks (such as banking licensing, money transmission, or card network requirements) and/or a demonstrated track record of ramping quickly on complex regulatory context in a new domain
• Familiarity with statutory benefits/compensation/equity requirements in EMEA, APAC, or LATAM jurisdictions
• Experience launching People/Total Rewards programs in a new country or legal entity
• Experience with M&A integrations on the People side
• PMP, Lean/Six Sigma, or comparable structured-program training

Preferred Qualifications

• Experience with financial regulatory or licensing frameworks (such as banking licensing, money transmission, or card network requirements)
• Familiarity with statutory benefits/compensation/equity requirements in EMEA, APAC, or LATAM jurisdictions
• Experience launching People/Total Rewards programs in a new country or legal entity
• Experience with M&A integrations on the People side
• PMP, Lean/Six Sigma, or comparable structured-program training

Location

• Office locations: New York, South San Francisco HQ, Seattle, or Chicago
• Remote locations: Remote in United States