HopSkipDrive
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 use AI every day, and not as a productivity add-on. It's woven into how we work at every level. We're rethinking how work gets done, who does what, and what a small team can accomplish. If you've already built AI into how you work, you'll hit the ground running. If you haven't, you'll need to be ready to learn fast and work differently than you have before. 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. You know how to work across Product and Sales to get to something that is defensible and drives the market. You're genuinely AI-forward. You’ve changed how you work because you are curious, you are an AI adopter and you know how to lead a team through that same shift. You think about redesigning workflows, what AI makes possible that wasn’t previously possible, and how to improve outputs before you think about what headcount would solve. You're a clear thinker and a direct communicator. You can hold the strategic narrative and get into the details when the work demands it. You build teams that trust each other, hold each other accountable, and don't confuse activity with outcomes. What you bring 10+ years of B2B marketing experience, with at least 3 years owning the full marketing function at a company with a complex sales cycle. Deep product marketing background: you've built and owned positioning, messaging, competitive strategy, pricing and packaging, go-to-market launches, and sales enablement that demonstrably changed how a sales team sells. Demonstrated accountability to pipeline and revenue metrics. You've held targets, not just reported against them, and you measure your work in marketing-sourced revenue, CAC, and time to revenue, not impressions or MQLs. Experience building or scaling a revenue marketing function, including marketing operations, attribution, and the data infrastructure to connect marketing investment to outcomes. A genuine track record of using AI to redesign workflows, drive team efficiency and productivity, and the ability to lead others through that shift. Experience marketing to institutional or public-sector buyers (school districts, government agencies, nonprofits or similarly complex, multi-stakeholder environments) is a strong plus, as is direct experience owning or building an RFP function. Strong executive communication skills; comfortable presenting to a board and investors, influencing at the C-suite level, and representing HopSkipDrive externally. Experience in a growth-stage, VC-backed company where resources are finite and speed matters. 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, mission-driven VC-backed company in a hugely attractive space with significant upside potential. HopSkipDrive is proud to operate as a drug-free workplace. HopSkipDrive is committed to fair and equitable compensation practices. The salary range for this role is $200,000–$250,000 + bonus. This position is primarily remote, with a strong preference for candidates in the LA area. Final compensation will be determined by relevant work experience, skill set, certifications, and specific work location. The total compensation package 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.