Risk Team Lead / Director

WithCoverage • Philadelphia, NY

5d

About The Position

WithCoverage is an AI-enabled risk management company serving high-growth businesses across industries. It combines risk advisors with proprietary technology to provide visibility into policies, exposures, claims, billing, and commissions. The company was founded by JD Ross and Max Brenner and has raised more than $43 million from investors including Sequoia, 8VC, Khosla Ventures, and Crystal Venture Partners.

The Risk Team Lead / Director will lead the strategy and execution of client risk advisory, helping clients understand, mitigate, and transfer risk across their portfolios. This role partners with advisors, service teams, and executive leadership to deliver risk solutions that support retention, growth, and operational excellence. The position is based in New York, NY, or Philadelphia, PA.

The successful candidate will manage a growing team of Risk Advisors, oversee client servicing and new placements, and lead the development of risk management programs across industries and lines of business. The role also contributes to team development and the improvement of processes, tools, and technology. The stated U.S. expected OTE range at the start of employment is $200,000–$300,000 per year; additional variable compensation, including quota-based incentives where applicable, may be available.

Requirements

• 8–12 years of experience in commercial insurance or risk management, ideally in a brokerage or consulting environment.
• At least 2 years of quota-carrying people-management experience, ideally in a fast-paced, high-ownership environment.
• Deep understanding of commercial lines, including general liability, property, auto, workers’ compensation, umbrella, and specialty.
• Ability to communicate complex insurance concepts clearly to executive-level clients in an advisory tone.
• Strong analytical and strategic thinking, with the ability to work across clients and industries.
• Leadership mindset and desire to mentor others and build scalable systems for growth.

Nice To Haves

• CPCU, ARM, CIC, or CRM designation.

Responsibilities

• Oversee client retention, client servicing, and new client placements across the Risk Advisory Team.
• Manage a growing team of Risk Advisors and ensure conversion, execution, and servicing timelines are met.
• Monitor and address Risk Team performance metrics and ensure expectations are met across a growing client base.
• Maintain high standards for 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, including property and casualty, workers’ compensation, auto, and cyber.
• Partner with Risk Advisors to deliver renewal and risk mitigation strategies.
• Oversee loss analysis, benchmarking, and claims trends to guide client decisions and carrier negotiations.
• Evaluate client operations, exposures, and contractual risks and propose proactive solutions.
• Support internal education and the development of best practices across the risk team.
• Collaborate with leadership to improve processes, tools, and technology for risk advisory delivery.

Benefits

• Equity grants.
• Medical, dental, vision, life, and disability benefits.
• Pre-tax accounts, including FSA, HSA, dependent care FSA, and commuter savings.
• 401(k) through Human Interest.
• Flexible time off and sick leave.
• Family and medical leave.
• Major national holidays.
• Curated in-office employee experience designed to foster community, team connections, and innovation.
• Competitive compensation and potential variable compensation, including quota-based incentives where applicable.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed