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
You will be our first dedicated Workplace and People Operations hire, helping shape how our company runs and how it feels to work here. This is not just about keeping things organized. You will build the foundation for our employee experience as we scale, from how the office operates to how every new hire starts their journey. Role Overview
This is a high-impact role based in our NYC office at the center of the company. You will own the day-to-day workplace experience while supporting core People Operations workflows across onboarding, systems, and employee lifecycle processes. You will partner across teams to ensure things run smoothly, people feel supported, and processes scale with the business. If you enjoy building from the ground up and being the person who makes everything work, this role will be a great fit. What You’ll Own
Workplace and Office Operations
Make our NYC office run smoothly and feel like a great place to work
Manage vendors including facilities, cleaning, snacks, and supplies
Plan and coordinate team events and in-office moments
Support seating and workspace planning as the team grows
Handle day-to-day logistics including mail, access, and inventory
Onboarding and Employee Experience
Own onboarding logistics for all new hires
Ensure every new hire is set up for success on day one
Partner with Recruiting and hiring managers to deliver a strong onboarding experience
Run onboarding sessions and continuously improve the experience
People Operations
Manage employee data and workflows in Rippling
Support onboarding and offboarding processes and documentation
Handle employee requests and employment verifications
Partner with Finance or vendors to support payroll and bonus inputs
Maintain employee records including agreements and policies
Support training programs and track completion
Equipment and Systems
Coordinate laptop setup and inventory management
Partner with IT vendors to ensure employees are fully set up
Maintain clean, organized systems and process documentation
What Success Looks Like
The NYC office runs smoothly and feels organized, welcoming, and high quality
New hires have a seamless and thoughtful onboarding experience
People Operations processes are reliable, clear, and easy to follow
Employees know where to go for support and get help quickly
You Might Be a Fit If
You have 2 to 5 years of experience in office operations, HR coordination, or People Ops
You are highly organized and detail-oriented
You are a strong communicator and enjoy working with people across teams
You are comfortable using systems like HRIS platforms and Google Suite
You are proactive, resourceful, and comfortable in a fast-paced environment
You have experience with Rippling or a similar HR system
You have supported onboarding or employee lifecycle processes
You have worked in a startup or high-growth environment
If you are the type of person who takes pride in making things run smoothly and creating a great experience for others, you will have a meaningful impact here from day one
For candidates based in the United States, the expected pay range for this position at the start of employment is $60,000 – $75,000/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
