Job description

At HopSkipDrive, our goal is to create opportunity for all through mobility.

We’re a technology company that solves complex transportation challenges where there is a heightened need for safety, equity, and care. Through our marketplace, we connect kids, older adults, or anyone needing extra support to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts around the country.

Founded by three moms as a solution to their own transportation challenges, we’ve now facilitated more than 3.3 million rides and operate across over 13 states across the country. We continue to expand at a rapid pace, making the Inc. 5000 list four times, as well as the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a Series D company and has raised $100M in funding to date.

Who We Are

As the Director of Insurance, Risk, and Litigation you will be responsible for overseeing HopSkipDrive’s insurance and loss control programs and litigation matters. This includes reviewing and assessing claims and litigation to mitigate and manage risk for HopSkipDrive, as well as executing on litigation matters in connection with external counsel. With cross-functional partners, this role will strategically oversee HopSkipDrive’s insurance portfolio and renewals, and support with risk exposure analyses for existing and new services so that HopSkipDrive business partners can make informed decisions.

The ideal candidate for this role will be a highly organized, detail-oriented attorney with a proven track record in developing litigation, risk and insurance functions in-house. Given the cross-functional nature of this role, it is expected that this individual is well versed in how to provide counsel to cross functional teams in a way that is collaborative, clear and concise, and puts the needs of the business first.

The following duties will be performed under the direction of the SVP of Legal & Policy:

In partnership with external counsel, oversee litigation matters and advise HopSkipDrive on the best courses of action with respect to litigation matters. (estimated 30%)
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. (estimated 40%)
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. (estimated 30%).
As needed, will eventually perform management duties including but not limited to hiring, training, evaluating, coaching, and developing direct reports.

Who You Are

You are a strategic thinker always looking for ways to improve HopSkipDrive’s risk profile. With the following skills, you’ll make a tangible and immediate impact:

J.D. from an accredited law school
Experience managing litigation in-house
Experience with insurance counseling and managing an insurance portfolio, with transportation and/or transportation network company or delivery network company experience strongly preferred
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, with prior people management experience being helpful to support future growth

Our Investment In You

We want you to be an owner in our company and share in executing our vision, so every full-time employee has equity. In addition, we offer flexible vacation, medical, dental, vision and life insurance, 401(k), FSA, and an opportunity to work for a uniquely positioned, VC-backed company in a hugely attractive space with significant upside potential. HopSkipDrive is committed to fair and equitable compensation practices. The salary range for this role in Los Angeles, CA is $180,000.00 - $200,000.00 This position is remote and, as such, compensation will ultimately be in line with the location in which the position is filled. Final compensation for this role will be determined by several factors such as a candidate’s relevant work experience, skill set, certifications, and specific work location. The total compensation package for this role also includes equity stock options.

HopSkipDrive is proud to be an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or any other protected class.

* This role will be fully remote in one of the following states AZ, CA, CO, CT, DC, FL, GA, IL, IN, KS, MA, MD, MI, MN, MO, NC, NJ, NM, NV, NY, OH, OK, OR, SC, TN, TX, UT, VA, WA, WI**

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