Director, Insurance, Risk, Litigation

Summary

Join HopSkipDrive as the Director of Insurance, Risk, and Litigation, overseeing insurance programs, loss control, and litigation matters. You will manage litigation, advise on strategic courses of action, and oversee the insurance portfolio, ensuring alignment with business objectives. This role involves providing strategic counsel to cross-functional partners on risk assessment for existing and new services. The ideal candidate is a highly organized attorney with in-house litigation and insurance management experience. You will collaborate with external counsel and cross-functional teams, making data-driven decisions to mitigate risk and support business growth. This remote position offers competitive compensation, equity, and benefits.

Requirements

• J.D. from an accredited law school
• Experience managing litigation in-house
• Experience with insurance counseling and managing an insurance portfolio
• 13+ years of experience in relevant fields of law including any combination of litigation, insurance, and general in-house counseling
• Ability to make complex decisions by gathering cross-functional input
• Ability to act independently to develop and enforce procedures
• Proven ability to present proposals/recommendations with a strong opinion and a clear point of view, backed with data, that includes outcomes, timelines and owners
• Experience managing consultants

Responsibilities

• In partnership with external counsel, oversee litigation matters and advise HopSkipDrive on the best courses of action with respect to litigation matters
• Oversee HopSkipDrive’s insurance program and portfolio in line with business objectives and sound risk management principles, successfully execute insurance renewals, help identify the products and services that will best mitigate loss, advise HopSkipDrive on insurance and claims management strategies, advise HopSkipDrive on insurance coverage to best balance risk with business financial and brand objectives, and maintain relationships with insurance brokers and insurers
• Provide strategic counseling to cross-functional business partners on existing and new services with a lens toward understanding and quantifying potential risk in order to help the business make informed decisions
• As needed, will eventually perform management duties including but not limited to hiring, training, evaluating, coaching, and developing direct reports

Preferred Qualifications

• Experience with insurance counseling and managing an insurance portfolio, with transportation and/or transportation network company or delivery network company experience strongly preferred
• Prior people management experience being helpful to support future growth

Benefits

• Equity
• Flexible vacation
• Medical, dental, vision and life insurance
• 401(k)
• FSA
• Opportunity to work for a uniquely positioned, VC-backed company in a hugely attractive space with significant upside potential
• Equity stock options
• Remote work