People Operations Lead

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 relationships, mail handling, and facilities coordination
• Manage the full employee equipment lifecycle: procurement, setup, inventory tracking, and retrieval at off boarding
• Coordinate with the IT vendor to ensure every employee is fully set up and supported from day one; serve as the internal point of contact for system access and tooling questions
• Manage office budget, vendor contracts, and seating strategy as the team grows
• Own setup and logistics for all-hands meetings, team events, and in-office programming

What Success Looks Like

• New hires describe their onboarding as one of the best they have experienced
• People Operations processes are reliable, documented, and easy to navigate for employees and managers alike
• The Rippling HR Services transition is clean and complete by August 2026, with no gaps in payroll, compliance, or employee data
• The NYC office runs at a consistently high standard -- organized, welcoming, and off everyone else's plate
• Leadership trusts you to own this function independently and sees you as a key partner in scaling the company
• You are building toward something: as the People function grows, so does this role

You Might Be a Fit If

Experience and Skills

• You have 3 or more years of experience in People Operations, HR Operations, or program management, ideally at a high-growth startup
• You have owned an HR function or program end-to-end -- not just supported it -- and have the instincts and judgment to show for it
• You have deep, hands-on experience with Rippling or a comparable HRIS platform, including building automations and workflows
• You have designed or significantly improved an onboarding program from scratch
• You are a systems thinker who builds processes that scale, not just solve today's problem
• You have strong project management skills and can run multi-stakeholder initiatives with minimal direction
• You are highly organized, detail-oriented, and rigorous about accuracy in sensitive data
• You have strong written and verbal communication skills and present ideas and processes with clarity
• You are comfortable owning office operations, admin, and facilities as part of a broader People Ops remit

Who You Are

• You thrive in fast-paced, build-it-yourself environments. You are energized by ambiguity, not slowed by it
• You are an owner. You find the gaps, build the solutions, and do not wait to be told what to fix
• You have high emotional intelligence -- self-aware, empathetic, and effective in cross-functional collaboration
• You are ambitious and curious. You care deeply about what you do and find joy in solving problems others find hard
• You are collaborative, organized, thoughtful, and kind

For candidates based in the United States, the expected pay range for this position at the start of employment is $100,000 – $125,000/year. Actual compensation will be determined based on factors such as market location, job-related skills, experience, and qualifications. This role may also be eligible for additional variable compensation, including quota-based incentives where applicable. WithCoverage offers a comprehensive Total Rewards package for full-time employees, which includes equity grants and a robust suite of benefits.

What We Offer:

• Competitive compensation that includes equity
• Comprehensive benefit plans for medical, dental, vision, life, and disability
• Pre-tax accounts (FSA, HSAs, dependent care FSAs, commuter savings)
• Human Interest: 401(k) provider
• Time Off: Flexible time off, sick leave, family and medical leave, major national holidays
• A curated in-office employee experience, designed to foster community, team connections, and innovation
• Collaborative, transparent, and fun culture