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.

About The Role:

As our Billing Manager, you’ll own day-to-day billing execution, keeping invoices accurate, payments moving, and customers well supported. This is a hands-on individual contributor role for someone who enjoys solving problems and building reliable processes. You’ll coordinate with billing service partners and work closely with Risk, Finance, and Product to improve the billing experience as WithCoverage grows.

What You’ll Do:

• Handle daily billing activities, including invoicing, payment application, collections, and account maintenance, with a focus on accuracy and timely service.
• Coordinate with billing service partners, communicate priorities, monitor quality and turnaround times, and resolve service issues.
• Resolve escalated billing questions, overdue balances, and exceptions in partnership with customers, carriers, and internal teams.
• Document billing procedures and work with colleagues and service partners to deliver consistent, reliable service.
• Partner with Finance on reconciliations, billing reporting, and month-end support, ensuring discrepancies are investigated and resolved.
• Track billing performance and strengthen processes and controls to reduce errors, improve collections, and support growth.
• Work with Risk and Product to improve billing workflows, reduce manual work, and support changes to systems and processes.

Who You Are:

• Experience in billing, accounts receivable, or financial operations, including responsibility for day-to-day execution and process improvement.
• Insurance billing experience strongly preferred, particularly in a brokerage or agency environment.
• Experience coordinating billing workflows and working with service partners to maintain quality and resolve issues.
• Strong analytical skills and attention to detail, with confidence using spreadsheets and billing or accounting systems to investigate discrepancies.
• Clear communication and sound judgment, with a customer-service mindset and the ability to work across teams on complex billing issues.
• A hands-on, organized approach and the ability to balance daily priorities with longer-term improvements in a growing business.

For candidates based in the United States, the expected pay range for this position at the start of employment is $100,000 – $120,000/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, and major national holidays
• A curated in-office employee experience, designed to foster community, team connections, and innovation
• Collaborative, transparent, and fun culture