People Operations Lead

About this role

People Operations Lead

Location: New York, NY

About WithCoverage :

WithCoverage replaces the traditional insurance brokerage with AI-supercharged risk management designed for the modern economy.

We partner with hundreds of high-growth, category-defining companies, including GoPuff, Eight Sleep, Bombas, Chomps, and Blank Street Coffee. Our clients span iconic consumer brands, hospitality leaders, GCs, advanced manufacturers, and next-generation defense contractors. They operate in complex risk environments and need a partner that can move at their speed.

Instead of a fragmented, manual brokerage stack, we have built a new category: elite risk advisors operating on top of proprietary technology. Our in-house Agency Management System gives our team and AI agents full visibility into policies, exposures, claims, billing, and commissions. This platform enables deep automation, better decisions, and a fundamentally higher standard of service.

WithCoverage was founded by JD Ross (co-founder of Opendoor) and Max Brenner (Bain, Compound). We have raised over $43M from leading investors including Sequoia, 8VC, Khosla Ventures and Crystal Venture Partners.

Our ambition is not to build a better brokerage. It is to redefine how risk is managed across the economy.

Why Join Us:

• Grow Faster – We’re scaling quickly, giving you significant opportunities to learn, lead, and shape your career and the company's future.

• Work That Matters – We protect the world’s most innovative brands: consumer icons, hospitality leaders, next-gen defense contractors, and US manufacturers.

• Redefine an Industry – Insurance is one of the largest, slowest-moving markets. We rewrite the playbook with proprietary technology, automation, and AI.

• Financial Rewards – We hire the best and invest in you. That means competitive comp, meaningful equity, and excellent benefits. We believe strongly in internal promotion and lay out a plan for everyone's career growth.

Why This Role

This is a rare opportunity to be the first dedicated People Operations hire at a high-growth company redefining an industry. You will not inherit a playbook -- you will write it.

The People Operations Lead owns the infrastructure behind our employee experience: the systems that power how every person joins, grows, and thrives at WithCoverage. People Ops is the core of this role. You will also own our NYC office operations, admin, and facilities -- absorbing work currently fragmented across the team so that our leaders can focus on what they do best.

This role sits at the center of the company and reports to our Head of Talent.

What You’ll Own

• People Programs and Systems

• New Hire Onboarding: Own and evolve the onboarding experience end-to-end, from offer acceptance through the first 90 days -- prioritizing personalization, clarity, and scalability so every new hire feels set up for success

• Design and facilitate new hire orientations: People (HR, benefits, time off, referrals), Founder (vision, values, what we sell), product walkthrough, and systems setup

• Build and maintain onboarding materials, checklists, and a company wiki so information is always current and easy to find

• Partner with Recruiting and hiring managers to continuously raise the bar on the onboarding experience

• Performance and Engagement: Drive execution of performance review cycles; manage engagement survey delivery and communications; interpret results and surface insights to leadership

• People Tools and Systems: Own and administer Rippling as the system of record -- maintaining data integrity, building automations, and ensuring clean, audit-ready records

• Co-lead the transition from our current HR Ops vendor to Rippling HR Services (launching August 2026), owning the workflows, documentation, and employee communication

• Own ongoing HRIS management: status changes, off boarding workflows, employment verifications, and system configuration as we scale

• People Data and Workflows: Build and manage workflows for tracking all people changes throughout the year -- promotions, role changes, terminations, and off boarding -- ensuring systems and records are always accurate

• HR Knowledge Base: Launch and maintain a centralized resource for employees and managers covering onboarding, off boarding, benefits, policies, and compliance

• Benefits and Compliance

• Benefits Administration: Lead management of our benefits programs, including open enrollment coordination, vendor relationships, employee education, and day-to-day issue resolution

• Payroll Inputs: Partner with Finance on payroll inputs, bonus processing, and reimbursements -- owning accuracy at every step

• HR Compliance: Maintain compliance with applicable employment requirements, policies, and documentation across our NYC office and US remote population; escalate complex matters as needed

• Employee Records: Maintain all employee records, agreements, and HR documentation in a well-organized, compliant manner

• Employee Experience and Culture

• Employee Engagement: Design and run engagement initiatives that reinforce culture, connection, and retention across our NYC office and remote team

• Recognition: Own our birthday, work anniversary, and milestone recognition program

• Internal Communications: Manage employee guides and wiki; build communication plans for People programs so the team is always informed and supported

• Manager Support: Serve as a People Ops partner to people managers -- providing guidance on performance conversations, feedback, and day-to-day people management questions

• Develop and maintain clear manager resources, templates, and documentation to support consistent management practices

• Office Operations, Admin, and Facilities

Our NYC office needs a dedicated owner. This is not the primary lens of the role, but it is real work that should run seamlessly in the background.

• Own the day-to-day NYC office experience: supplies, snacks, catering, vendor relationshi

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