Risk Team Lead ​/ Director

With Coverage is reimagining risk management and insurance for the modern economy. We protect the companies building the future—100's of brands like GoPuff, Eight Sleep, Bombas, Chomps, and Blank Street Coffee—so they can move fast without compromise.

Instead of a stale brokerage model, we’ve built a new category: world-class risk advisors powered by proprietary technology. From next-generation defense contractors and advanced manufacturers to iconic consumer brands and hospitality leaders, we partner with ambitious businesses to give them the confidence to scale.

Founded by JD Ross (co-founder of Opendoor) and Max Brenner (Compound, Bain), With Coverage is disrupting a trillion-dollar industry from the inside out. We grew 10x last year while staying cash-flow positive, with backing from 8VC, Crystal Venture Partners, and other top investors.

We’re also the only brokerage that has built its own Agency Management System from scratch, giving us full control of our operations and a platform to automate more and more of the business with AI. It’s the foundation for transforming how risk is managed across the economy.

• Grow Faster – We’re scaling fast, giving you outsized opportunities to learn, lead, and shape your career and the future of the company.
• 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 great benefits. We believe strongly in internal promotion, and lay out a plan for everyone's career growth.

As the Director of Risk Management, you’ll lead our strategy and execution for client risk advisory, helping clients understand, mitigate, and transfer risk across their portfolios. You’ll partner closely with advisors, service teams, and executive leadership to deliver world‑class risk solutions that drive retention, growth, and operational excellence.

• Directly responsible for client retention, client servicing, and oversight on new client placements across With Coverage’s Risk Advisory Team
• Manage a growing team of Risk Advisors to ensure all conversion, execution, and servicing timelines are met.
• Monitor and address performance metrics with Risk Team to ensure performance expectations are met across a rapidly growing client base.
• Maintain a culture of excellence across the Risk Team as it pertains to day to day work, client engagement, and internal operational execution.
• Lead the design and implementation of client risk management programs across multiple industries and lines of business (P&C, Workers Comp, Auto, Cyber, etc.)
• Partner with Risk Advisors to deliver comprehensive renewal and risk mitigation strategies
• Partner with Risk Advisors to oversee loss analysis, benchmarking, and claims trends to guide client decision‑making and carrier negotiations
• Partner with Risk Advisors to evaluate client operations, exposures, and contractual risks to propose proactive solutions
  
  Support internal education and development of best practices across the risk team
• Collaborate with leadership to enhance processes, tools, and technology for risk advisory delivery

• 8–12 years of experience in commercial insurance or risk management, ideally within a brokerage or consulting environment
• 2+ years of quota carrying-people management experience, ideally in a fast paced and high ownership environment
• Deep understanding of commercial lines (GL, Property, Auto, WC, Umbrella, and Specialty)
• Proven ability to communicate complex insurance concepts to executive-level clients in a clear, advisory tone
• Strong analytical and strategic thinker, comfortable working across clients and industries
• Leadership mindset with a desire to mentor others and build scalable systems for growth
• Designations (CPCU, ARM, CIC, CRM) preferred but not required

For candidates based in the United States, the pay range for this position at the start of…