Director, Head of Communications

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.

What you will do

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.

What We’re Looking For

• 10-12+ years of communications experience, with a tenure in the technology sector.

• A comprehensive understanding of the media landscape and a proven track record in securing top-tier and local earned media and building strong press relationships.

• Demonstrated, expert-level experience in both policy and crisis communications is a must.

• Proven experience leading and developing a high-performing communications team and managing PR agencies.

• Exceptionally strong writing, organization, and communication skills, with the ability to distill complex ideas into clear, compelling narratives.

• A team-player attitude with the ability to work independently, influence stakeholders, and manage complex issues effectively.

• A passion for HopSkipDrive's mission to create opportunity for all through mobility.

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 base salary range for this role is $180,000 - $200,000. 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 in which we actively hire in: 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**