Vice President, Marketing

HopSkipDrive is hiring a remote Vice President of Marketing to lead our B2B marketing organization and drive growth into new markets. This is a full-time position reporting directly to our CEO, where you'll build and lead a revenue-focused marketing engine for our multi-stakeholder marketplace. We offer competitive compensation including $200,000–$250,000 salary plus bonus, equity for all full-time employees, flexible vacation, comprehensive medical, dental, vision, and life insurance, 401(k), and FSA.

Position Summary

HopSkipDrive operates a marketplace connecting schools, districts, government agencies, and nonprofits with vetted caregivers, supported by software that solves transportation logistics challenges. Our B2B marketing must address both institutional buyers controlling budgets and end-users whose satisfaction influences purchasing decisions. As VP of Marketing, you'll lead the complete go-to-market strategy, drive pipeline growth, and scale our market presence.

Day-to-Day Responsibilities

• Own the complete marketing organization: brand positioning, demand generation, field marketing, events, proposal management, customer advocacy, product marketing, sales enablement, and customer lifecycle growth.
• Lead product marketing as a strategic discipline with market research, competitive positioning, go-to-market campaigns, pricing strategy, and sales enablement that improves deal velocity.
• Build a marketing strategy where every investment connects to pipeline, revenue, and retention—not vanity metrics.
• Own the proposal and RFP process in partnership with Sales as a strategic competitive capability.
• Lead demand generation across digital channels and events, where events drive meaningful acquisition and relationships.
• Establish and protect brand strategy, messaging consistency, and positioning across all external touchpoints.
• Partner with Sales and Customer Success on ideal customer profiles, pipeline targets, lead quality standards, and expansion signals.
• Build a customer lifecycle and expansion marketing program focused on churn reduction, account growth, and improved net revenue retention.
• Oversee marketing technology, attribution, lead scoring, and data infrastructure enabling revenue accountability.
• Integrate AI throughout the marketing organization to increase productivity and scale impact without proportional headcount growth.
• Manage the marketing budget with rigor on ROI, customer acquisition cost, and marketing-influenced revenue.

What We're Looking For

• 10+ years in B2B marketing with at least 3 years owning the full marketing function at a company with a complex sales cycle.
• Deep product marketing background with positioning that wins in competitive markets, messaging that sales teams use, and enablement that improves deal outcomes.
• Proven accountability to pipeline and revenue metrics, measured through marketing-influenced revenue and customer acquisition cost.
• Experience building or scaling a revenue marketing function including marketing operations, attribution, and data infrastructure.
• Track record using AI to redesign workflows and leading teams through that transformation.
• Comfort presenting to boards, influencing executives, and representing the company externally.
• Experience in venture-backed, growth-stage companies where resources are constrained and speed matters.
• Experience marketing to institutional buyers or complex multi-stakeholder environments is a strong plus, as is RFP ownership.

About the Company

Founded by three parents to solve real transportation challenges, HopSkipDrive has facilitated over five million rides across twenty-plus states. We're on the Inc. 5000 list multiple times and recognized on the Deloitte 500 list of fast-growing technology companies. As a Series D company that has raised $100M, we have strong market recognition, a mature product, and ambitious growth plans. We're deeply AI-forward—all team members actively use AI tools and embrace learning new approaches. We operate as a remote-first, mission-driven organization where outcomes matter more than activity.

How to Apply

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