Senior Director of Risk Management

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 and advisory services, 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

Our emerging Risk team is focused on both mitigating and managing risks in order to continue to fulfill HopSkipDrive’s mission.  As the leader of this newly formed function, you will support the business in the following ways:

• Lead HopSkipDrive’s insurance program and portfolio in line with business objectives and sound risk management, including maintaining strong relationships with insurance brokers and insurers, finding ways to best position the company to prospective insurers, advising HopSkipDrive on insurance strategy including the formation of a captive, advising HopSkipDrive on coverage amounts to best balance risk with business financial and brand objectives.  
• Own, analyze, and make recommendations to improve HopSkipDrive’s claims handling process
• Work closely with HopSkipDrive leaders to understand and manage strategic, financial, and operational risk
• Develop HopSkipDrive’s overall risk management strategy and objectives, and promote organization-wide understanding of risks and risk management strategies through trainings, reporting, and policy development/oversight
• Implement a reporting process to inform senior leadership of risk- related issues and opportunities
• Work to quantify risk with existing and new service offering in order to best advise HopSkipDrive in decisions relating to its products and services
• 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:

• Experience building a risk management function at a rapidly-scaling start up company, with prior marketplace company experience strongly preferred
• 10+ years of experience in risk management
• A recognized leader with strong executive presence, dynamic and proactive decision making skills, and the ability to adapt well to and initiate change within an organization
• Ability to formulate and execute on strategic plans in line with company objectives
• Ability to optimize operational efficiency and effectiveness, and make decisions in complex situations using data and key stakeholders' input
• 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
• Prior management experience and experience building a team from the ground up
• Bachelor’s degree and relevant licenses/qualifications in risk management

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 $175,000 - $220,000. 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**