Jobs at Alumni Ventures Portfolio Companies


Director of CareDriver Engagement



Posted on Saturday, May 20, 2023

Who we are

HopSkipDrive’s mission is to create opportunity for all through mobility. Our safe, innovative youth transportation solution is used by over 450 school districts, charter schools, non-profits and government agencies, and busy families to get kids where they need to go.

With nearly 500,000 yellow buses on the road every day and 3.5 billion miles driven a year, student transportation is the largest mass transit system in the US. And while districts spend $25 billion annually on transportation, only 30% of kids get to school on a bus every day. Add to the equation a crippling bus driver shortage and increasing needs for individualized transportation solutions, and it is clear the current system is expensive, inefficient, and ripe for disruption.

We create personalized transportation solutions from one to many, and everything in between.

We’re a company with heart

Our partnerships with school districts, child welfare agencies, and nonprofits ensure equitable educational access for our most vulnerable populations, including youth in foster care, youth experiencing homelessness, and youth with special needs.

We understand that the difference between struggle and success can sometimes be as simple as the ability to show up, which is why we’re on a mission to use innovative technology, coupled with operational expertise and new thinking to help kids reach their full potential by providing a safe, dependable way to get them where they are going.

We’re an awesome place to work

Our company culture has been well-recognized — HopSkipDrive has been named Fast Company Most Innovative Companies, Best Places to Work lists from Built in LA, Comparably, Inc., and the Los Angeles Business Journal. Comparably also named us to the Best Company for Professional Development, Best CEO, and Best CEOs for Women lists.

We’re growing rapidly

Founded by three moms as a solution to their own transportation challenges, we now serve 12 states and 22 metros across the country and continue to expand at a rapid pace, twice making the Inc. 5000 and Deloitte 500 Fast-Growing Technology lists. Backed by top-tier venture capital firms, HopSkipDrive has raised $100M in funding to date.

Who you are

You are looking for a challenging and rewarding experience. You are inspired by our vision and the opportunity to define a new category in an incredibly fast-growing market. You are excited to learn, grow and collaborate so we can achieve our mission of creating opportunity for all through mobility.

At HopSkipDrive, we know that challenges require different approaches, unique perspectives and new ways of thinking. We are building a team of creative problem-solvers from many different backgrounds.

You thrive in a fast-paced startup environment. You are honest and exhibit high integrity. You are proactive and excited to bring new ideas to the company. You solicit feedback and are open to criticism. You adjust quickly to changes in priorities and conditions and cope effectively with complexity and change. You have high attention to detail.

You are an excellent communicator who enjoys collaborating with others above all, you want to build something that fundamentally changes the lives of families for the better. As a Director of CareDriver Engagement your role will be to nurture and support our CareDriver community to deliver continuous improvement in overall ride quality, as well as enhancements to CareDriver acquisition, CareDriver productivity, and CareDriver retention.

What You'll Do

  • You will pay a key role in evolving and maintaining our HopSkipDrive CareDriver certification requirements
  • You will work cross-functionally across Supply, Product, Sales, Legal, and Business Operations to set and communicate requirements
  • You will work with CareDriver Ops to maintain the processes to efficiently build supply to set standards
  • Own and operate marketplace configurations to maximize efficiency of supply and demand matching
  • Operate in a highly fluid environment, think creatively, structure problems analytically, prioritize rigorously, and use data to drive decision
  • Responsible for the health of our CareDriver community focussing on maximizing the extrinsic and intrinsic benefits that CareDrivers obtain within our community through building opportunities for CareDrivers to:
    • Create a sense of belonging amongst CareDrivers
    • Provide paths for deeper participation in the HopSkipDrive Mission and Value
    • Create meaningful milestones for CareDrivers as they increase their participation in the community, and celebrate those events across the community
    • Cross-functionally manages the Community Building Project plan to include Product, Supply, Sales, Legal and Operations
    • Identify and experiment with new CareDriver initiatives
    • Independently sets goals and KPIs for each initiative you spearhead and provide regular reporting on progress against those metric
  • Owns what it means to be qualified as a CareDriver in every market, for every contract
    • Expert on state, local, contract, and internal requirements for CareDrivers
    • Own and evolve CareDriver qualification standards, including advanced qualifications
    • Evolve standards to support market launches and new contracts
    • Build and maintain all documentation on qualification standards, including training and reference materials for Sales, Marketing, and CareDriver Operations
    • Partner with Legal, Sales, and Supply to identify RFP and contract requirements that are outside of current CareDriver qualification standards, and assess the feasibility and cost of meeting the
  • Own and drive operational tasks related to company initiatives impacting the CareDriver population
  • Recommend audits and updated certification requirements when notified of regulatory or contractual changes
  • Assist with special projects as needed

What you bring:

  • An A+ player who is building a challenging and rewarding career
  • Change/Culture Management experience
  • Matrix management skills and matrix team leadership experience
  • 5+ years of operational experience
  • Experience developing and executing strategic initiatives
  • Exceptional analytical, investigative, and organizational skills
  • You bring a passion for data-driven decision making and are an analytical powerhouse
  • You are an Excel/ Google Sheets power user: you build complex, elegant models containing layers of advanced formulas (nested logic, offsets, index/match, etc.), simple assumptions and crystal clear dashboards to drive business insights both for other data nerds and less technical audience
  • Proficiency with Tableau

** This role will be fully remote from a state where we do business AZ, CA, CO, DC, FL, IL, KS, MD, WI, NC, NV, NJ, NY, OR, TX, SC, UT, VA, MI, MO, TN, NM, WA**

What you will get

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 is $90,000 to $110,000. 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.

Equal Opportunity Employer

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. HopSkipDrive is also proud to operate as a drug-free workplace.