About The Position

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. Who We Are 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.

Requirements

  • 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.

Nice To Haves

  • 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.

Responsibilities

  • 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.

Benefits

  • equity
  • flexible vacation
  • medical
  • dental
  • vision
  • life insurance
  • 401(k)
  • FSA
  • stock options
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