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HopSkipDrive

Trust & Safety Investigator

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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 you are

Our Trust and Safety team focuses on maintaining platform safety through proactive education, effective incident response, and crisis management to ensure a trustworthy ride experience. As a Trust & Safety Investigator, you will be responsible for maintaining all aspects of HopSkipDrive's investigative processes related to safety incidents. This role is critical in maintaining HopSkipDrive values and ensuring that any issues are thoroughly investigated and resolved promptly. This role requires a strategic thinker with an analytical mindset, and a deep commitment to upholding safety and integrity. You will respond to critical incidents and emergencies, including accidents, natural disasters, and security threats, ensuring timely and effective resolution. You are passionate about safety and are never happy with the status quo. You are always ready with ideas, motivated to continually improve the safety of our community, and drive a culture of safety and compliance. 

You Will: 

  • Conduct detailed investigations into safety and emergency incidents, Zero Tolerance Policy violations, and other operational concerns
  • Collect, analyze, and interpret data from various sources to support investigation findings
  • Prepare detailed reports of investigation findings and provide recommendations for corrective actions
  • Provide support for collisions and escalations; own insurance claim handling
  • Maintain accurate and confidential records of all investigations
  • Collaborate with other teams within the Trust & Safety organization, as well as cross-functional teams such as Safe Ride Support, Client Experience, and Sales, to gather necessary information and ensure comprehensive investigations
  • Communicate investigation outcomes to relevant stakeholders including senior management
  • Stay current with industry best practices and legal requirements related to safety and investigations
  • Support the Regional Case Managers in managing caseloads and prioritizing investigations
  • Be an advocate for platform safety and support both sides of the Marketplace

You Have: 

  • 2+ years of experience directly related to Trust & Safety
  • 2+ years of experience in investigations, claims management, risk assessment, or a related field; experience in the transportation or tech industry is a plus 
  • Outstanding written and verbal communication skills across multiple functions and teams
  • Ability to exercise business judgment to manage sensitive and complex escalations
  • Experience working with diverse stakeholders, from executives to front-line workers
  • A creative problem solver with the ability to work independently
  • Bachelor’s degree in Criminal Justice, Business, Data Science, or a related field is a plus 
  • Direct experience in Rideshare or a similar two-sided marketplace is preferred

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 is $65,000 - $77,000 annually, 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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HopSkipDrive Los Angeles, California, USA Office

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