Head Of People Operations Jobs in Illinois
Head Of People Operations jobs in Illinois are open across Chicago, Schaumburg, and Lisle and other Illinois metros, with employers like Zurich Insurance, Arthur J. Glatfelter Agency, and Cushman & Wakefield hiring at every experience level. Find a role that fits below and apply directly.
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INTRODUCTION
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
Stripe's mission is to increase the GDP of the internet — and we do that responsibly. The User Risk Strategy (URS) function is at the heart of that responsibility: it is the team that defines who Stripe can do business with, on what terms, and how those standards are maintained and enforced at scale. The function sits within the First Line of Defense in Stripe's Risk organization and is the authoritative owner of Stripe's supportability framework. We are looking for a seasoned leader to own and evolve the URS / Supportability function as a Manager of Managers (M2). In this role, you will lead a team of risk strategists and analysts across Ecosystem Strategy, New Product Enablement, User Insights & Enablement, Platform Risk Strategy, and Enforcement & Monitoring Strategy (EMS). You will be a senior leader in the Risk Strategy organization, shaping the direction of Stripe's supportability ecosystem and driving cross-functional decisions that directly influence Stripe's ability to grow safely. In this role, you will report into the Head of Risk Strategy and partner closely with Product, Engineering, Legal, Financial Crimes, Financial Partnerships, Operations, and GTM leadership.
ROLE AND RESPONSIBILITIES
What you’ll do
Responsibilities
Strategy & Vision:
- Own the long-term vision and strategy for Stripe's User Risk / Supportability function, ensuring legitimate users can use Stripe while protecting Stripe's financial platform, brand, and regulatory standing.
- Translate Stripe's business objectives and risk appetite into a cohesive, multi-year supportability strategy that balances risk exposure with user experience.
- Define the risk/reward framework for new industry enablement and new product enablement — setting the standard for how Stripe evaluates and expands access responsibly.
- Develop and execute a clear roadmap across the URS organization that is aligned to Stripe's SOKRs and articulated to senior leadership.
Ecosystem Strategy:
- Own Stripe's global Terms of Service standards — the Supportability Handling Guide — including restricted and prohibited business categories.
- Set the strategic direction for how Stripe's supportability ecosystem evolves as Stripe's product footprint and geographic reach expand.
- Be the final decision-maker on policy changes that carry meaningful risk exposure or require cross-functional alignment, and represent Risk's position with Legal, FinCRO, card networks, and external partners.
- Integrate financial partner Restricted/Prohibited Business Lists (RBL/PBL) into Stripe's policy framework.
New Product Enablement:
- Lead the strategy and approval process for new product enablement — developing the appropriate RBL/PBL strategy for new products and incorporating new bank partner requirements.
- Ensure that risk standards are embedded early in the product development lifecycle, partnering with Product and Engineering to shape how supportability is implemented in new Stripe products.
- Work with Legal and Financial Partnerships to assess and integrate compliance obligations introduced by new products and banking relationships.
User Insights & Enablement:
- Lead the strategy for new industry enablement — evaluating emerging and underserved industries for supportability, and developing the frameworks that allow Stripe to access these markets responsibly.
- Own the Large User Advisory function, providing structured, high-quality guidance on complex user-specific supportability questions — enabling GTM and Partnerships to unlock revenue while managing risk appropriately.
- Develop scalable frameworks for advisory decisions so the function can handle growing volume without compromising quality.
Platform Risk Strategy:
- Lead Platform Risk Strategy, which covers large user requests, health monitoring, and education for Stripe's largest and most complex users.
- Develop scalable approaches to managing the supportability risk profile of Stripe's largest platforms and complex use cases, providing clear guidance and risk frameworks to internal stakeholders.
- Drive education and self-service capabilities so that internal teams and users can navigate Stripe's supportability standards more independently.
Enforcement & Monitoring Strategy (EMS):
- Provide strategic direction to the EMS team, which is responsible for integrating Stripe's supportability standards into detection and enforcement systems.
- Ensure that URS standards are operable, enforceable, and continuously tuned based on performance data and insights.
- Partner with Engineering, Product, and Data Science to develop data-driven detection strategies, improve enforcement precision, and reduce false positives that create unnecessary user friction.
- Maintain global EMS coverage, including regional strategy across North America and EMEA/APAC.
People & Organizational Leadership:
- Lead and develop a team across five sub-teams, including multiple team-level managers (M0/M1) and senior individual contributors.
- Set a high bar for talent and actively recruit, develop, and retain excellent risk strategists.
- Build a team culture grounded in Stripe's Operating Principles — one that is analytically rigorous, user-centric, and collaborative.
- Coach and develop your direct reports to grow in both their functional craft and their leadership capabilities.
- Build succession depth and develop a clear talent strategy for the function.
Cross-Functional Leadership:
- Act as the senior Risk Strategy voice in cross-functional risk forums, product reviews, and partner negotiations relevant to supportability.
- Partner with Product and Engineering on the Supportability platform, influencing the roadmap to ensure our systems accurately reflect policy intent and scale effectively.
- Work with GTM and Partnerships to develop scalable access to supportability information, reducing friction in the sales cycle while maintaining risk discipline.
- Engage with Legal and Financial Partnerships on policy positions, regulatory changes, and external partner requirements.
- Represent URS at senior Risk leadership reviews and provide clear, data-backed narrative on the state of the supportability ecosystem.
- Drive cross-functional programs with impacts across Risk and the broader organization — including Third Party Agent (TPA) programs, Actor-Level Enforcement, and strategic GTM/URS collaboration initiatives — ensuring clear goals, DRIs, and measurable outcomes.
MINIMUM QUALIFICATIONS
We're looking for someone who meets the minimum requirements to be considered for the role. If you meet these requirements, you are encouraged to apply. The preferred qualifications are a bonus, not a requirement.
- 10+ years of experience in risk strategy, policy, compliance, or a related field, with deep experience in user/merchant risk, supportability, or financial services regulation.
- 4+ years of people management experience, including managing managers; demonstrated ability to lead through multiple layers of an organization.
- Proven track record of owning and evolving complex policy or standards frameworks at scale, ideally within a payments, fintech, or marketplace context.
- Demonstrated ability to deliver at scale — you have built systems, frameworks, and teams that operate well beyond individual effort, and you instinctively design for leverage and repeatability across large, complex organizations.
- Champion for AI and automation — you actively seek opportunities to apply AI-powered tooling and automation to accelerate risk strategy work, reduce manual toil, and improve the quality and consistency of decisions at scale; you set the example for your team in adopting and driving these capabilities.
- Exceptional cross-functional collaborator — you know how to build trust with Legal, Engineering, Product, Sales, and Operations, and can reconcile competing stakeholder views to drive results.
- Analytical rigor — you are comfortable with data and can structure risk/reward trade-offs clearly and compellingly for senior audiences.
- Executive presence and clear written and verbal communication — you can distill complex risk topics into actionable narratives for leadership.
PREFERRED QUALIFICATIONS
- Experience working with card network rules (Visa, Mastercard), financial partner compliance requirements, or regulatory frameworks relevant to payments (e.g., BIN sponsorship, direct acquiring).
- Familiarity with supportability or trust & safety systems, detection and enforcement tooling, or risk policy automation.
- Experience in a high-growth technology company managing risk at scale.
LOCATION
This role is available either in an office or a remote location (35+ miles or 56+ km from a Stripe office).
In-office expectations
Office-assigned Stripes spend at least 50% of the time in a given month in their local office or with users. This hits a balance between bringing people together for in-person collaboration and learning from each other, while supporting flexibility about how to do this in a way that makes sense for individuals and their teams.
Working remotely at Stripe
A remote location is defined as being 35 miles (56 kilometers) or more from one of our offices. While you would be welcome to come into the office for team/business meetings, on-sites, meet-ups, and events, our expectation is you would regularly work from home rather than a Stripe office. Stripe does not cover the cost of relocating to a remote location. We encourage you to apply for roles that match the location where you currently live or plan to live.
PAY AND BENEFITS
The annual US base salary range for this role is $184,000 - $276,000. For sales roles, the range provided is the role’s On Target Earnings ("OTE") range, meaning that the range includes both the sales commissions/sales bonuses target and annual base salary for the role. This salary range may be inclusive of several career levels at Stripe and will be narrowed during the interview process based on a number of factors, including the candidate’s experience, qualifications, and location. Applicants interested in this role and who are not located in the US may request the annual salary range for their location during the interview process.
Additional benefits for this role may include: equity, company bonus or sales commissions/bonuses; 401(k) plan; medical, dental, and vision benefits; and wellness stipends.
INTRODUCTION
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
Stripe's mission is to increase the GDP of the internet — and we do that responsibly. The User Risk Strategy (URS) function is at the heart of that responsibility: it is the team that defines who Stripe can do business with, on what terms, and how those standards are maintained and enforced at scale. The function sits within the First Line of Defense in Stripe's Risk organization and is the authoritative owner of Stripe's supportability framework. We are looking for a seasoned leader to own and evolve the URS / Supportability function as a Manager of Managers (M2). In this role, you will lead a team of risk strategists and analysts across Ecosystem Strategy, New Product Enablement, User Insights & Enablement, Platform Risk Strategy, and Enforcement & Monitoring Strategy (EMS). You will be a senior leader in the Risk Strategy organization, shaping the direction of Stripe's supportability ecosystem and driving cross-functional decisions that directly influence Stripe's ability to grow safely. In this role, you will report into the Head of Risk Strategy and partner closely with Product, Engineering, Legal, Financial Crimes, Financial Partnerships, Operations, and GTM leadership.
ROLE AND RESPONSIBILITIES
What you’ll do
Responsibilities
Strategy & Vision:
- Own the long-term vision and strategy for Stripe's User Risk / Supportability function, ensuring legitimate users can use Stripe while protecting Stripe's financial platform, brand, and regulatory standing.
- Translate Stripe's business objectives and risk appetite into a cohesive, multi-year supportability strategy that balances risk exposure with user experience.
- Define the risk/reward framework for new industry enablement and new product enablement — setting the standard for how Stripe evaluates and expands access responsibly.
- Develop and execute a clear roadmap across the URS organization that is aligned to Stripe's SOKRs and articulated to senior leadership.
Ecosystem Strategy:
- Own Stripe's global Terms of Service standards — the Supportability Handling Guide — including restricted and prohibited business categories.
- Set the strategic direction for how Stripe's supportability ecosystem evolves as Stripe's product footprint and geographic reach expand.
- Be the final decision-maker on policy changes that carry meaningful risk exposure or require cross-functional alignment, and represent Risk's position with Legal, FinCRO, card networks, and external partners.
- Integrate financial partner Restricted/Prohibited Business Lists (RBL/PBL) into Stripe's policy framework.
New Product Enablement:
- Lead the strategy and approval process for new product enablement — developing the appropriate RBL/PBL strategy for new products and incorporating new bank partner requirements.
- Ensure that risk standards are embedded early in the product development lifecycle, partnering with Product and Engineering to shape how supportability is implemented in new Stripe products.
- Work with Legal and Financial Partnerships to assess and integrate compliance obligations introduced by new products and banking relationships.
User Insights & Enablement:
- Lead the strategy for new industry enablement — evaluating emerging and underserved industries for supportability, and developing the frameworks that allow Stripe to access these markets responsibly.
- Own the Large User Advisory function, providing structured, high-quality guidance on complex user-specific supportability questions — enabling GTM and Partnerships to unlock revenue while managing risk appropriately.
- Develop scalable frameworks for advisory decisions so the function can handle growing volume without compromising quality.
Platform Risk Strategy:
- Lead Platform Risk Strategy, which covers large user requests, health monitoring, and education for Stripe's largest and most complex users.
- Develop scalable approaches to managing the supportability risk profile of Stripe's largest platforms and complex use cases, providing clear guidance and risk frameworks to internal stakeholders.
- Drive education and self-service capabilities so that internal teams and users can navigate Stripe's supportability standards more independently.
Enforcement & Monitoring Strategy (EMS):
- Provide strategic direction to the EMS team, which is responsible for integrating Stripe's supportability standards into detection and enforcement systems.
- Ensure that URS standards are operable, enforceable, and continuously tuned based on performance data and insights.
- Partner with Engineering, Product, and Data Science to develop data-driven detection strategies, improve enforcement precision, and reduce false positives that create unnecessary user friction.
- Maintain global EMS coverage, including regional strategy across North America and EMEA/APAC.
People & Organizational Leadership:
- Lead and develop a team across five sub-teams, including multiple team-level managers (M0/M1) and senior individual contributors.
- Set a high bar for talent and actively recruit, develop, and retain excellent risk strategists.
- Build a team culture grounded in Stripe's Operating Principles — one that is analytically rigorous, user-centric, and collaborative.
- Coach and develop your direct reports to grow in both their functional craft and their leadership capabilities.
- Build succession depth and develop a clear talent strategy for the function.
Cross-Functional Leadership:
- Act as the senior Risk Strategy voice in cross-functional risk forums, product reviews, and partner negotiations relevant to supportability.
- Partner with Product and Engineering on the Supportability platform, influencing the roadmap to ensure our systems accurately reflect policy intent and scale effectively.
- Work with GTM and Partnerships to develop scalable access to supportability information, reducing friction in the sales cycle while maintaining risk discipline.
- Engage with Legal and Financial Partnerships on policy positions, regulatory changes, and external partner requirements.
- Represent URS at senior Risk leadership reviews and provide clear, data-backed narrative on the state of the supportability ecosystem.
- Drive cross-functional programs with impacts across Risk and the broader organization — including Third Party Agent (TPA) programs, Actor-Level Enforcement, and strategic GTM/URS collaboration initiatives — ensuring clear goals, DRIs, and measurable outcomes.
MINIMUM QUALIFICATIONS
We're looking for someone who meets the minimum requirements to be considered for the role. If you meet these requirements, you are encouraged to apply. The preferred qualifications are a bonus, not a requirement.
- 10+ years of experience in risk strategy, policy, compliance, or a related field, with deep experience in user/merchant risk, supportability, or financial services regulation.
- 4+ years of people management experience, including managing managers; demonstrated ability to lead through multiple layers of an organization.
- Proven track record of owning and evolving complex policy or standards frameworks at scale, ideally within a payments, fintech, or marketplace context.
- Demonstrated ability to deliver at scale — you have built systems, frameworks, and teams that operate well beyond individual effort, and you instinctively design for leverage and repeatability across large, complex organizations.
- Champion for AI and automation — you actively seek opportunities to apply AI-powered tooling and automation to accelerate risk strategy work, reduce manual toil, and improve the quality and consistency of decisions at scale; you set the example for your team in adopting and driving these capabilities.
- Exceptional cross-functional collaborator — you know how to build trust with Legal, Engineering, Product, Sales, and Operations, and can reconcile competing stakeholder views to drive results.
- Analytical rigor — you are comfortable with data and can structure risk/reward trade-offs clearly and compellingly for senior audiences.
- Executive presence and clear written and verbal communication — you can distill complex risk topics into actionable narratives for leadership.
PREFERRED QUALIFICATIONS
- Experience working with card network rules (Visa, Mastercard), financial partner compliance requirements, or regulatory frameworks relevant to payments (e.g., BIN sponsorship, direct acquiring).
- Familiarity with supportability or trust & safety systems, detection and enforcement tooling, or risk policy automation.
- Experience in a high-growth technology company managing risk at scale.
LOCATION
This role is available either in an office or a remote location (35+ miles or 56+ km from a Stripe office).
In-office expectations
Office-assigned Stripes spend at least 50% of the time in a given month in their local office or with users. This hits a balance between bringing people together for in-person collaboration and learning from each other, while supporting flexibility about how to do this in a way that makes sense for individuals and their teams.
Working remotely at Stripe
A remote location is defined as being 35 miles (56 kilometers) or more from one of our offices. While you would be welcome to come into the office for team/business meetings, on-sites, meet-ups, and events, our expectation is you would regularly work from home rather than a Stripe office. Stripe does not cover the cost of relocating to a remote location. We encourage you to apply for roles that match the location where you currently live or plan to live.
PAY AND BENEFITS
The annual US base salary range for this role is $184,000 - $276,000. For sales roles, the range provided is the role’s On Target Earnings ("OTE") range, meaning that the range includes both the sales commissions/sales bonuses target and annual base salary for the role. This salary range may be inclusive of several career levels at Stripe and will be narrowed during the interview process based on a number of factors, including the candidate’s experience, qualifications, and location. Applicants interested in this role and who are not located in the US may request the annual salary range for their location during the interview process.
Additional benefits for this role may include: equity, company bonus or sales commissions/bonuses; 401(k) plan; medical, dental, and vision benefits; and wellness stipends.
See All 9 Head Of People Operations Jobs in Illinois
Find roles in Illinois that match your experience and apply in just a few clicks.
Find JobsHead Of People Operations Jobs by City in Illinois
Where Illinois roles are concentrated, by current openings.
Head Of People Operations Job Market in Illinois
A snapshot from current Illinois openings, updated as new roles post.
Who's Hiring
- Zurich Insurance2
- Arthur J. Glatfelter Agency1
- Cushman & Wakefield1
- Fidelity Investments1
- Google1
Top Industries Hiring
- Insurance3
- Banking & Financial Services1
- Construction & Real Estate1
- Fintech1
- Investment & Asset Management1
What Illinois Employers Look For
The qualifications that appear most often in head of people operations jobs across Illinois.
- 7 or more years of progressive HR leadership experience, including managing HR teams
- Demonstrated experience building or scaling people programs across the full employee lifecycle
- Proficiency with an HRIS platform such as Workday, BambooHR, or Rippling
- Bachelor's degree in human resources, business administration, organizational psychology, or a related field
- Experience developing and executing talent acquisition, retention, and workforce planning strategies
- SHRM-SCP, SPHR, or equivalent senior HR certification preferred by many employers
Head Of People Operations Jobs in Illinois: Frequently Asked Questions
How many head of people operations jobs are there in Illinois?
There are 9+ head of people operations openings in Illinois on Migrate Mate as of June 2026, with the most roles in Chicago, Schaumburg, and Lisle. New positions post regularly as employers across Illinois hire.
How much do head of people operationses make in Illinois?
Head of people operationses in Illinois earn a median of about $151,370 a year, based on May 2025 Bureau of Labor Statistics wage data, ranging from around $90,820 for the lowest 10% to over $267,520 for the top 10%. Pay rises with experience, specialty, and employer.
Which Illinois cities have the most head of people operations jobs?
Chicago, Schaumburg, and Lisle have the most head of people operations openings in Illinois right now, with additional roles spread across smaller metros statewide.
Which companies hire head of people operationss in Illinois?
Employers hiring head of people operationss in Illinois include Zurich Insurance, Arthur J. Glatfelter Agency, and Cushman & Wakefield, based on current listings on Migrate Mate as of June 2026.
Are there remote head of people operations jobs in Illinois?
Yes. About 56% of head of people operations openings tied to Illinois are remote or hybrid as of June 2026. The rest are on-site roles based in Illinois metros.
How do I apply for head of people operations jobs in Illinois?
You can apply to head of people operations jobs in Illinois directly on Migrate Mate. Search the listings above, find roles that match your experience and preferred Illinois location, then apply to each one that fits.
See All 9 Head Of People Operations Jobs in Illinois
Find roles in Illinois that match your experience and apply in just a few clicks.
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