About

WithCoverage:

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

We partner with over one thousand 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 Business Operations Lead, you will work directly with executive leadership and partner closely with Risk and Product to redesign how Risk Management is delivered. You will build the systems that determine how work flows through the organization, how teams are structured, and how performance is measured.

This is not a role where you hand off recommendations. You will own problems from diagnosis through implementation, starting with the details of how the work gets done, then deploying solutions across the organization.

What You’ll Do:

• Develop a deep, end-to-end understanding of how the Risk team operates - from client request through final output - including handoffs, bottlenecks, and differences across industries such as construction, consumer goods, and technology.
• Identify the highest-leverage opportunities to improve quality, speed, and efficiency, then lead the work required to capture them.
• Define the metrics that reveal performance, capacity constraints, and operational breakdowns across the Risk organization.
• Build the reporting and capacity-planning systems used to inform hiring, resource allocation, and performance management across Risk pods.
• Design and continuously improve the standard operating procedures that guide the Risk team as our organization and technology evolve.
• Determine the right ownership model for critical workflows, including team structures, responsibilities, and new role profiles.
• Partner closely with Product to translate operational pain points into a prioritized roadmap for automation and technology investment.

Who You Are:

• You have 4+ years of experience in rigorous strategy and operations roles, such as management consulting and/or early stage operations.
• You are an exceptional structured problem solver who can build context quickly, form clear hypotheses, and use data to reach practical conclusions.
• You have high agency. You are comfortable defining the path forward when the problem is ambiguous and the information is incomplete.
• You combine systems thinking with a willingness to get into the details of workflows, data, and day-to-day execution.
• You are motivated by building solutions that work at 10x the current scale, not simply fixing the immediate problem.
• You can move independently from analysis to implementation while keeping senior leaders aligned.
• You communicate clearly and can influence teams across functions, even when you do not have formal authority.

For candidates based in the United States, the expected pay range for this position at the start of employment is $150,000 – $185,000/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