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 five million rides across over 17 states around 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.
The New Markets team is a fast-moving, high-impact group focused on launching and scaling operations in new regions. We are looking for an analytical, adaptable, and proactive operator to join our team and own the end-to-end success of our marketplace performance.
- Own near-term supply and demand forecasts for launch markets by designing and maintaining predictive models aligned to company directives.
- Operate and optimize marketplace configurations, including zip code mapping and cluster assignments, to maximize supply-demand matching efficiency.
- Design, build, and ship targeted productivity promotions to address fill rate gaps, manage market spend, and drive operational efficiency.
- Evaluate market health by monitoring net revenue and contribution margin, recommending cross-functional remediation for struggling markets.
- Monitor performance trends proactively, identifying root causes of off-track metrics and bringing forward data-backed recommendations.
- Own end-to-end project workstreams by defining scope, identifying owners, tracking progress, and ensuring cross-functional execution.
- Leverage AI-assisted workflows to accelerate research, monitor territory performance, and pressure-test strategic recommendations.
Who You Are
You are a high-agency operator who thrives in ambiguous environments and possesses a relentless drive to solve complex operational challenges. You have a proven track record of managing stakeholders, utilizing data to influence outcomes, and building scalable processes from the ground up.
- 3+ years of experience driving superior results in analytical, cross-functional, or operations roles, ideally in marketplace, logistics, or high-growth environments.
- Excel/Google Sheets power user capable of building complex, elegant models with advanced formulas and dashboards that work for non-technical stakeholders.
- Demonstrated ability to make nuanced business decisions based on imperfect information while remaining accountable for the outcomes.
- Proven ability to lead projects involving stakeholders who do not report to you, aligning teams and resolving friction to drive closure.
- Strong communication skills with the ability to translate complexity for different functions and levels without losing precision.
- High agency in identifying necessary actions and executing them independently in a fast-moving environment.
- Experience independently pulling and structuring data, with comfort using SQL or other data querying tools.
- Working knowledge of Tableau; expected to grow in report-building and contribute to team dashboards
- Demonstrated comfort using AI tools (such as Claude, ChatGPT, Perplexity, or equivalent) as an integral part of your actual daily workflow.
- You’ll flex across the full lifecycle of a launch — from infrastructure setup to cross-functional coordination to performance monitoring — doing whatever it takes to get a city operational and on a path to contribution margin positive.
- This is not a role for people who wait for direction. It’s for operators who identify gaps, build the tools to close them, and hold themselves accountable to outcomes.
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 proud to operate as a drug-free workplace. HopSkipDrive is also committed to fair and equitable compensation practices. The salary range for this role is 95,000 - 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.
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, DC, FL, GA, IL, IN, KS, MA, MD, MI, MN, MO, NC, NJ, NM, NV, NY, OK, OR, SC, TN, TX, UT, VA, WA, WI** Prioritizing candidates in Eastern and Southeast states based on business needs.
