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Job Overview
Location
Remote
Job Type
Full-time
Category
Marketing
Date Posted
December 23, 2025
Full Job Description
đź“‹ Description
- • Own the full-cycle sales motion for large K-12 school districts and government transportation agencies across the Midwest, managing pipelines from first discovery to signed multi-year contracts worth $500K–$5M+ ARR.
- • Develop and execute a territory plan that prioritizes the 100 highest-value prospects in Illinois, Indiana, Ohio, Michigan, Wisconsin, and Missouri, mapping decision-makers, funding cycles, and procurement calendars to hit quarterly and annual revenue targets.
- • Lead consultative discovery workshops with superintendents, transportation directors, special-education leaders, and procurement officers to surface pain points such as driver shortages, budget constraints, and safety compliance gaps, then translate those insights into tailored HopSkipDrive solutions.
- • Build compelling business cases backed by ROI models, case studies, and pilot projections that demonstrate how our CareDriver marketplace and SaaS platform reduce costs, improve on-time performance, and expand equitable access for vulnerable student populations.
- • Orchestrate virtual and on-site presentations, multi-stakeholder demos, and reference calls that bring our safety protocols, driver-vetting technology, and real-time visibility tools to life for skeptical public-sector buyers.
- • Negotiate complex master service agreements, data-security addenda, and insurance requirements with district legal teams and state cooperatives, ensuring every clause aligns with both client risk tolerance and HopSkipDrive margin goals.
- • Partner cross-functionally with Solutions Engineering, Legal, Finance, and Customer Success to craft SOWs, pricing tiers, and implementation timelines that set new accounts up for rapid launch and long-term expansion.
- • Maintain meticulous CRM hygiene in Salesforce, logging activities, forecasting revenue within 5 % accuracy, and providing executive leadership with real-time visibility into deal risk, competitive threats, and upsell opportunities.
- • Champion market feedback to Product and Marketing, surfacing feature gaps, competitive intelligence, and emerging funding sources that inform roadmap decisions and regional campaign messaging.
- • Represent HopSkipDrive at state school-board conventions, transportation conferences, and equity-focused symposiums, establishing thought-leadership presence that generates inbound pipeline and elevates our mission-driven brand.
- • Mentor junior Account Executives and SDRs by sharing best-practice playbooks, objection-handling techniques, and negotiation strategies that elevate overall team performance and culture.
- • Deliver on an annual new-logo revenue quota of $3–4 M while maintaining a 3x pipeline coverage ratio and a win rate above 30 % on qualified opportunities.
🎯 Requirements
- • 5+ years of quota-carrying enterprise or strategic sales experience selling SaaS, marketplace, or transportation solutions to public-sector or highly regulated clients
- • Proven track record of closing contracts ≥ $500K ARR and exceeding $2 M annual quotas in a remote-first environment
- • Deep familiarity with K-12 or municipal procurement processes, RFP cycles, and state contracting vehicles
- • Ability to travel 25–40 % across the Midwest for on-site meetings, demos, and negotiations
- • Bachelor’s degree in Business, Public Policy, or related field (MBA or advanced degree a plus)
🏖️ Benefits
- • Remote-first culture with quarterly in-person team summits in destinations like Denver and Los Angeles
- • Competitive OTE of $250K+ with uncapped commission accelerators and equity in a high-growth Series D company
- • 100 % employer-paid medical, dental, and vision insurance for employees and 80 % for dependents
- • 12 weeks fully paid parental leave and flexible PTO policy that actually encourages time off
- • Annual professional-development stipend of $3,500 for conferences, certifications, or continued education
Skills & Technologies
Remote
About HopSkipDrive Inc.
California-based safe youth transportation company providing scheduled rides for children aged 6-17 through a technology platform that matches families, schools and government agencies with fully vetted and monitored CareDrivers using their own cars. Services include home-to-school, school-to-activities and foster care mobility solutions, supported by real-time tracking, strict safety protocols and compliance expertise for school districts and child welfare organizations nationwide.
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