Director of Specialty Transportation

Who we are

HopSkipDrive’s mission is to create opportunity for all through mobility. Our innovative, supplemental school transportation solutions are used by over 600 school districts, charter schools, nonprofits, government agencies, as well as busy families to safely and reliably get kids where they need to go.

Student transportation is the largest mass transit system in the U.S. The way kids get to and from school has a direct impact on our kids, families, schools and communities. While school districts spend $28 billion annually on transportation, only 30% of kids get to school on a bus. The current system can no longer meet all the transportation needs of our districts, schools and families — and its shortcomings are causing inequities in educational access that are affecting the welfare of millions of kids each day.

HopSkipDrive is taking a different approach to arranging safe, reliable school transportation that meets needs that aren’t being addressed by the current system, helping to fill gaps and supplement the student transportation options available. We create personalized transportation solutions for the one to the many, and everything in between.

We’re a company with heartOur partnerships with school districts, child welfare agencies and nonprofits ensure equitable educational access for the most vulnerable populations, including youth in foster care, children experiencing homelessness and students with disabilities. 

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 ways of 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 workOur company culture has been well-recognized — HopSkipDrive has been named to Fast Company’s Most Innovative Companies list, as well as Best Places to Work lists from Built In LA, Comparably, Inc., and the Los Angeles Business Journal. Comparably also named us a Best Company for Professional Development, as well as to its Best CEO and Best CEOs for Women lists.

We’re growing rapidlyFounded by three moms as a solution to their own transportation challenges, we now 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 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.

Your role 

As the Director of Specialty Transportation at HopSkipDrive, you will report directly to our SVP of Growth and be the business owner of a critical, new category for our business. School districts arrange transportation for hundreds of thousands of students everyday who require highly specialized vehicles, equipment or supports.  This includes many students with disabilities who require a wheelchair lift-equipped vehicle, a safety vest or second adult in the car,  early childhood students who require a car seat, and others students who are most efficiently routed on a 6-12 passenger van.    

You will establish this new vertical as an essential part of our care-based  mobility business, bringing the extraordinary level of safety, reliability and service our clients have come to expect from HopSkipDrive to their most complex needs.

What you'll do

Strategic leadership

• Be the business owner of the specialty transportation vertical, responsible for its growth, success and financial contribution to the company
• Become expert on how school districts solve specialty transportation challenges today - who does what, what works, what doesn’t, etc.
• Spend time with our customers, understand their motivations, fears, desires, etc, and bring the voice of the customer to a wide range of internal discussions 
• Map, size and constantly reassess the market as well as the competitive landscape and how we position within it
• Set strategic direction, constantly formulating and reformulating what we need to do and in what order to win the vertical 
• Develop and manage strategic partnerships, including with transportation providers 
• Lead the discovery and evolution of product-market-sales fit for new and existing products 
• Partner with our sales and marketing teams to develop and continuously iterate on go-to-market strategy

Drive internal execution

• Work closely with a large and diverse group of cross-functional partners (across product, sales, marketing legal, trust & safety, support and supply departments) and drive alignment on vision, strategy and tactics 
• Establish pilots with clear learning agendas and success criteria and drive execution to ensure delivery on objectives  
• Partner with our product and operational teams to develop and continuously iterate on the product vision and roadmap 

• Support the sales team in growing our customer base, directly participating in the sales cycle for strategic accounts
• Be the internal champion of the business; regularly communicate vision, strategy, and status a clear and compelling way to internal and external stakeholders  

What you’ll bring

An Entrepreneur

• No problem too big, no task too small.  Equally comfortable cold calling a 55+ living community as sitting down with a county commissioner as presenting an investment case to executives.  
• Comfort with ambiguity.  Doesn’t need to be handed a playbook to win the game.  Will start with first principles and navigate fluidly to an objective.   Independent and self-starting.   
• Divergent and strategic thinker.  Sees a problem from multiple angles, generates new ideas, balance of “what if…” and grounded in reality, nose for the wedge. 
• Scrappy.   One door gets slammed, find another.  

A Strong Communicator

• Communicates effectively with a wide range of external and internal stakeholders from diverse backgrounds 
• Produces a wide range of high-quality strategic assets with clear, crisp and compelling prose and visuals (PPT, Word, Google Suite, etc.)
• Confidently represents HopSkipDrive with clients, potential clients and ecosystem players

A Seasoned Cross-Functional Leader 

• Expertise using  informal influence rather than positional authority to drive aligned action with urgency through a range of cross-functional partners  
• Highly skilled initiative owner.  Wraps arms around complex and loosely defined business problems, backwards plans to success, defines roles, responsibilities and timelines, and ensures a large group delivers on commitments    

A Skilled and Driven Professional

• A+ player looking to build a challenging and rewarding career
• 7-10+ years experience driving superior results in highly analytical and strategic roles within fast-paced business environments.
• Intermediate to advanced Excel/Sheets and PowerPoint/Slides required
• Intellectual curiosity and a love of learning
• Highly organized and detail-oriented; ability to manage a wide range of responsibilities and switch quickly between divergent workflows 

Nice to have/Preferred:

• Existing network and expertise in some aspect of the specialty transportation space (e.g. NEMT, brokerage models, youth with disabilities, mobility, etc.)  
• Specific expertise in GTM strategy - market sizing, TAM/SAM/SOM, customer segmentation, ICP, personas, positioning, delivery channels, financial modeling, etc.  

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

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 is $150,000-170,000. This 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.