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Director, Head of Communications

HopSkipDrive
November 14, 2025

HopSkipDrive seeks a Director, Head of Communications.

Overview

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.

Responsibilities

You are a strategic, results-driven communications leader who thrives on the news and loves creating nuanced, objective-based messaging. You have a comprehensive understanding of the earned media landscape and a passion for shaping narratives. You are a natural leader and a team player, eager to roll up your sleeves to get the job done. You approach your work with drive, ownership, and empathy, and excel in ambiguous, fast-paced environments where you can cut through the noise and provide clear strategic recommendations. You have deep experience in the technology sector and are an expert in navigating complex policy, safety, and corporate situations. In this role, you will:

  • Set the Strategy: Develop and oversee the company's comprehensive communications strategy, leading all earned media, managing corporate messaging, and strategic initiatives.
  • Own the Narrative: Plan and execute proactive and reactive communications campaigns designed to raise HopSkipDrive’s profile, secure earned media, and shape understanding of the company among key audiences.
  • Lead in Crisis: Serve as a primary media contact and own the company's crisis communications function, including developing scenario plans, drafting statements, and briefing reporters on sensitive policy, safety, and corporate topics.
  • Build the Foundation: Create and manage a strategic messaging framework, and draft all foundational communications materials, including talking points, press releases, op-eds, and key messaging for company announcements.
  • Drive Execution: Lead the PR and communications strategy for all company announcements, coordinating cross-functionally with marketing, policy, safety, and leadership teams.
  • Navigate Complexity: Shape understanding of our legislative and regulatory priorities through strategic communications, working in close partnership with the Government Affairs team.
  • Build Your Team: Lead, mentor, and develop a high-performing communications team.

Learn More and Apply

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