Vice President, Marketing

About this role

About HopSkipDrive

At HopSkipDrive, our mission is to create opportunity for all through mobility. We're the leader in safe, fast, and simple supplemental student transportation. Through our marketplace, we connect kids to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts across 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 over 20states. We continue to grow rapidly — earning a spot on the Inc. 5000 list numerous times and the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a Series D company and has raised $100M to date.

How we work

We're an AI-forward company, and we expect every person on our team to be too. We use AI tools to do our best work — drafting, analyzing, building, and shipping faster than we could without them — and we invest in training, share what works, and govern AI use thoughtfully. We don't expect you to be an expert when you start. We do expect you to be curious, willing to learn, and ready to use the best tools available to move our mission forward.

We're remote-first, mission-driven, and built for people who want to do work that matters with people who hold a high bar.

Who we are

HopSkipDrive's go-to-market organization is the engine behind our growth. We sell to school districts, government agencies, and nonprofits — buyers who are mission-driven, relationship-dependent, and move on their own timeline. That means our marketing function has to do more than generate leads; it has to build the credibility, educate the market, and create the pipeline that a complex B2B sales cycle demands.

We're at an inflection point. We have strong brand recognition in our space, a maturing product, and an aggressive growth agenda. We are looking for a leader who can build a true revenue marketing function that operates in lockstep with Sales, is accountable to pipeline and revenue outcomes, and scales efficiently as we expand into new markets.

HopSkipDrive is a multi-sided marketplace. School districts, government agencies, and nonprofits are our buyers who organize and fund transportation for the students (and their parents) who use the service; and CareDrivers are caregivers on wheels who come to our platform to earn safe, flexible income.

As VP of Marketing, you will own the entire B2B marketing motion at HopSkipDrive. You will drive the full customer and user journey for our institutional buyers, who manage budgets and contracts, as well as the families and riders whose daily experiences heavily influence those buying decisions. You'll sit on our senior leadership team and report directly to the CEO.

Key responsibilities

• Own the full B2B marketing function: brand, demand generation, field and events marketing, RFPs, customer advocacy, product marketing, sales enablement, lifecycle and growth marketing.

• Lead product marketing as a core competency: market intelligence, client engagement and advocacy, competitive positioning, go-to-market launches, pricing and packaging strategy, and sales enablement that actually changes how a sales team sells. We use the Challenger methodology, and need someone familiar with how to sell, market, engage and communicate within that framework.

• Build and execute a revenue marketing strategy where every investment connects to pipeline, revenue, and retention outcomes, not traffic, impressions, or MQL volume.

• Drive the RFP function in partnership with Sales. This is a meaningful part of how we win new business in the public sector, and it needs to be treated as a strategic capability, not a reactive one.

• Own the entire demand gen engine, which is not only our digital channels but also includes events as one of our most important marketing channels.

• Oversee brand strategy and compliance across all external touchpoints, including earned media, events, digital, and content; serve as the steward of HopSkipDrive's voice and positioning.

• Partner tightly with Sales and Customer Success on ICP, pipeline targets, lead quality standards, and expansion signals; hold Marketing accountable to the same revenue goals Sales is held to.

• Build a lifecycle and growth marketing engine that reduces churn, drives expansion, and improves net revenue retention.

• Oversee the marketing tech stack, attribution, lead scoring, and the data infrastructure that makes revenue marketing possible.

• Drive the AI transformation of the marketing team’s capabilities, incorporating AI into every facet of the operating model. The expectation isn't that we grow our way to output; it's that we build AI into how the team works so we can scale impact without scaling headcount proportionally.

• Own the marketing budget and be rigorous about ROI, CAC, ROAS, and marketing-sourced revenue as the metrics that matter.

Who you are

• You've owned B2B marketing before, all of it, not just one function, but your foundation is in product marketing. You've built positioning that holds up in a competitive market (including against buyers who don't think they have a problem yet). You've crafted messaging that gives a sales team something real to say. You've created enablement that changed how deals get closed, not just the collateral library. You understand that "why us" is the hardest question in marketing to answer well, and you've demonstrably answered it well.

• You've also run the full funnel and you understand demand generation. You've held pipeline and revenue targets, and you know how to build programs that tie marketing investment to business outcomes. You measure your work in marketing-sourced revenue, CAC, and time to revenue, not clicks and impressions.

• Pricing and packaging isn't an afterthought for you. You've been in those conversations, you understand how those decisions ripple through positioning, sales conversations and competitive response

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