Risk Team Lead / Director

WithCoverage•Philadelphia, PA
•$200,000 - $300,000•Onsite

About The Position

WithCoverage is an AI-enabled risk management company that replaces the traditional insurance brokerage. Its proprietary Agency Management System provides visibility into policies, exposures, claims, billing, and commissions, supporting automation and risk-advisory services for high-growth companies across multiple industries. The Risk Team Lead / Director will lead strategy and execution for client risk advisory, helping clients understand, mitigate, and transfer risk across their portfolios. The role partners with advisors, service teams, and executive leadership to deliver risk solutions that support client retention, growth, and operational excellence. It is based in New York, NY or Philadelphia, PA.

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 comfort working 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

  • Take direct responsibility for client retention, client servicing, and oversight of 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 expectations across a growing client base.
  • Maintain a culture of excellence in day-to-day work, client engagement, and internal operational execution.
  • Lead the design and implementation of client risk management programs across 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.
  • Partner with Risk Advisors to oversee loss analysis, benchmarking, and claims trends to inform client decisions and carrier negotiations.
  • Partner with Risk Advisors to 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 benefit plans
  • Pre-tax accounts, including FSA, HSA, dependent care FSA, and commuter savings
  • 401(k)
  • Flexible time off
  • Sick leave
  • Family and medical leave
  • Major national holidays
  • Curated in-office employee experience designed to foster community, team connections, and innovation
  • Collaborative, transparent, and fun culture
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