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 completed 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

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.

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 $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.

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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