Director of People Operations and Systems

The mission

Whop is on a mission to deliver everyone a sustainable income. Today, 50,000 people make money on Whop every month, and Whop users are on track to earn more than $5 billion this year. We are building the infrastructure for the next generation of internet entrepreneurs, and we will keep going until one billion people earn money on Whop every month.

The role

Whop is growing quickly, and the systems behind our team need to move just as fast. We are hiring a hands-on operator to own People Operations and People Systems day to day. You will build and run the infrastructure that lets exceptional people join Whop, do their best work, and move with speed without sacrificing accuracy, trust, or compliance.

You will own the employee operating environment from signed offer through exit. That includes the systems, data, workflows, policies, and daily execution behind the employee experience. You will fix what is urgent today and help shape the roadmap for the company we are becoming.

You will work close to the details, automate aggressively, document what matters, and help grow the People Operations team as the company scales.

What you will own

• Run day-to-day People Operations, with clear priorities, service levels, and measures of success, and contribute to the People Operations roadmap alongside the Chief People and Talent Officer

• Execute the full employee lifecycle, including onboarding, employee changes, performance cycles, leaves, accommodations, work authorization, immigration support, offboarding, and records management

• Run payroll, benefits administration, and employment compliance, and manage policies, audits, and vendor relationships with a high bar for accuracy and employee trust

• Own the HRIS as the source of truth, including integrations, access controls, data quality, and simple, reliable workflows

• Build AI-enabled and self-service support that answers routine questions quickly, routes complex issues to the right owner, and reduces administrative work

• Build dashboards and reporting for headcount, hiring, retention, performance, and compensation so leaders can get accurate answers quickly

• Partner with the Chief People Officer to connect role approvals, recruiting operations, candidate data, offers, and onboarding into one seamless handoff

• Work with Finance, Legal, and IT on payroll, equity administration, compliance, security, and headcount data

• Write the operating playbooks Whop needs, then continuously simplify or automate them as the business changes

• Spot what will break next and fix it before growth turns it into a larger problem

What success looks like

In your first 90 days, you understand every critical workflow, system, owner, and employee pain point. You stabilize anything fragile and deliver a prioritized plan for People Operations and systems improvements.

Within six months, Whop has clean, reliable people data, a consistent employee lifecycle, clear service ownership, and a seamless handoff from recruiting through onboarding. Employees know where to go for help.

Within twelve months, core workflows are automated, payroll and benefits run cleanly, compliance is proactive, reporting informs decisions, and the function is ready to add headcount as Whop grows.

Who you are

• You have five or more years in People Operations, HR Operations, or People Systems, including experience owning major programs end to end, and ideally some experience managing or mentoring others

• You have helped build or scale People Operations at a high-growth technology company, ideally through a stage of roughly 100 to several hundred employees

• You have hands-on HRIS ownership, including implementations, integrations, permissions, vendor management, and ongoing optimization

• You know payroll, benefits, leaves, immigration, employee data, and US employment compliance well enough to run them accurately and know when to escalate or bring in counsel

• You are fluent in data and can turn an ambiguous question into a clear metric, analysis, and recommendation

• You use AI and automation as practical tools and can show where they improved speed, accuracy, or service

• You can fix a broken workflow in the morning and work through a sensitive employee case in the afternoon

• You communicate directly, exercise sound judgment, protect confidentiality, and earn trust across every level of the company

• You move quickly, take full ownership, and stay calm when priorities change

• You care more about building an exceptional company than following a traditional People playbook

How we work

Whop is an in office company of about 100 people. Most of the team are former founders and entrepreneurs. We give people real agency, meaningful resources, and ownership of hard problems. We expect everyone to move fast, tell the truth, and improve every surface they touch.

• Be technical. Your work should be correct, grounded in fact, and able to withstand scrutiny

• Force function. Solve the root cause and make the system materially better

• Disagree then commit. Debate hard before a decision, then execute together

The bar

We want someone who can run People Operations with the speed, rigor, and technical quality of Whop itself. We care less about the exact titles you have held and more about what you have built, how it held up under pressure, and whether you made the company meaningfully better.

What Whop offers

• Best in class cash compensation and meaningful equity

• A high trust environment with real ownership and direct access to company leaders

• The chance to build the People operating system for a company defining how the next generation earns a living

• Meals, wellness support, and office benefits designed for an in-person team

Equal opportunity

Whop is an equal opportunity employer. We consider qualified applicants without regard to race, color, religion, sex, national origin, age, disability, veteran status, sexual orientation, gender identity, or any other status protected by law. If you need a reasonable accommodation during the hiring process, let us know.