Project Manager, Total Rewards

Wwshemi; Chicago (IL); On-site; USD 140,000 - 190,000; Full time

Job summary

Stripe is hiring a Project Manager for Total Rewards to own end-to-end strategic programs across Benefits, Compensation, Equity, and M&A. You will partner with People, Finance, Legal, and Corporate Technology to drive high-impact outcomes and build scalable processes for a growing global team.

You will lead cross-functional initiatives, embed with pillar teams, and design repeatable program infrastructure while leveraging AI tools to accelerate work and improve stakeholder communications.

Qualifications

• 7+ years of People project, program, or operations management experience.
• Excellent written communication: executive updates, decision memos, playbooks.
• Strong stakeholder management across senior cross-functional partners.
• AI expertise: use AI for synthesis, drafting, analysis, communications.
• Analytical fluency: work with data to tell a credible story.
• Users-first mindset: focus on Stripe employee and operator experience.

Responsibilities

• Own end-to-end project management for high-profile Total Rewards projects, from intake to go-live.
• Advise and embed with project teams across Total Rewards and People portfolios.
• Build subject matter expertise across Benefits, Compensation, Equity, Talent Mobility, and M&A.
• Develop scalable program infrastructure: intake frameworks, SOPs, playbooks, handoff checklists.
• Leverage AI tools to accelerate synthesis, drafting, stakeholder communications, and docs.
• Drive cross-functional alignment with Legal, Finance, Corporate Tech, and others.
• Tackle complex questions with rigor, define approach, monitor progress, mitigate risks.
• Surface patterns across the portfolio and translate into recommendations for leadership.

Skills

People project management

Cross-functional collaboration

AI tooling familiarity

Written communication

Stakeholder management

Data analytics

User-centric mindset

Tools

Asana

Jira

Job description

Who we are

About Stripe

Stripe is a financial infrastructure platform for businesses. Millions of companies - from the world’s largest enterprises to the most ambitious startups - use Stripe to accept payments, grow their revenue, and accelerate new business opportunities. Our mission is to increase the GDP of the internet, and we have a staggering amount of work ahead. That means you have an unprecedented opportunity to put the global economy within everyone's reach while doing the most important work of your career.

About the team

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.

What you’ll do

Stripe's Total Rewards programs span compensation, benefits, equity, internal mobility/immigration, and mergers and acquisitions (M&A), each with cross-functional dependencies, regulatory stakes, and direct impact on the Stripes they affect. Delivering these programs well takes a Project Manager who develops real subject matter depth, engages with pillar leads as a strategic partner, and brings structure to decisions that aren't always clear-cut.

We're hiring a Project Manager to own high-priority Total Rewards projects and programs end to end. You'll work closely with our Benefits, Compensation, Equity, Talent Mobility, and M&A pillars, building expertise in how these programs work and what it takes to land them well. Some programs have established playbooks you'll sharpen; others are less defined and will need you to help shape the approach before you execute it. Across all of them, you'll identify dependencies early, proactively surface and mitigate risks, and keep complex, multi-stakeholder work moving toward clear outcomes. This is a high-leverage individual contributor role for someone who brings both rigor and judgment to every project they own.

Responsibilities

• Own end-to-end project management for high-profile cyclical and transformational Total Rewards projects, from intake and scoping through go-live and handoff to program owners
• Advise and embed with project teams across the Total Rewards and People portfolio, raising the quality bar and building PM capability across the extended team, not just doing the work yourself
• Build subject matter expertise across Benefits, Compensation, Equity, Talent Mobility, and M&A - becoming a reliable strategic thought partner to pillar teams on program decisions, not just a tracker of status
• Build, automate, and continuously improve the infrastructure that makes program management repeatable and scalable: intake frameworks, project plan templates, SOPs, playbooks, and handoff checklists for common program types
• Leverage AI tools in your daily work and the team's workflows, using them to accelerate synthesis, drafting, stakeholder communications, and documentation, and actively identifying new opportunities to work faster and better
• Drive cross-functional alignment across People and key partner functions (Legal, Finance, Corporate Technology, and others), creating shared visibility into priorities, dependencies, and blockers
• Tackle complex, ambiguous program questions with rigor and independence, owning work from problem definition through final recommendation - including defining the approach, monitoring progress, identifying risks early, and putting mitigation in place before issues land
• Surface patterns and gaps across the program portfolio, translating observations into structured analysis and recommendations for People leadership

Who you are

We're looking for someone who meets the minimum requirements to be considered for the role. The preferred qualifications are a bonus, not a requirement.

Minimum requirements

• 7+ years of People project, program, or operations management experience, including at least 3 years driving multi-stakeholder, cross-functional programs end to end, ideally at a scaling or global company
• A track record of building from scratch: you've created processes, playbooks, or program infrastructure where none existed before, not just improved what was already in place
• Excellent written communication: you can produce an executive update, a stakeholder decision memo, and a practitioner playbook with equal fluency
• Strong stakeholder management across senior cross-functional partners: you drive results with a balance of urgency and thoughtfulness, and know when to push, when to align, and when to elevate
• AI expertise: you default to AI tools for synthesis, drafting, analysis, and communications, and you proactively design workflows that help the team move faster and operate at scale.
• Analytical fluency: you can work with data to build a credible narrative, identify patterns across a program portfolio, and make recommendations grounded in evidence
• A users-first mindset: you obsess over the Stripe employee experience and the operator experience, not just the project/program artifacts

Preferred qualifications

• Familiarity with change management frameworks (such as Prosci ADKAR) and judgment about when to apply structured change management vs. lighter-touch approaches
• Experience building and deploying enablement materials or training resources for cross-functional teams
• Experience in Total Rewards, People Operations, or an adjacent HR domain
• Familiarity with PM and collaboration tools (Asana, Jira, or similar)
• Familiarity with Total Rewards or HR systems (such as Workday, equity administration platforms, or benefits administration tools)
• PMP, Lean/Six Sigma, or comparable structured-program training