Jobs at HopSkipDrive

Lead HopSkipDrive's full B2B marketing function, owning brand, demand generation, product marketing, RFPs, sales enablement, lifecycle/growth, and marketing operations. Build a revenue-focused, AI-enabled marketing organization accountable to pipeline, revenue, CAC and retention metrics; partner closely with Sales and Customer Success to drive expansion and measurable marketing-sourced revenue. Serve on the senior leadership team and report to the CEO.

The Data Analyst in Revenue Operations will analyze sales data, build models, and create reports using SQL, Excel, and BI tools to empower business decisions.

Administer and optimize Salesforce as the single source of truth; own the GTM tool stack and vendor lifecycle; design and build cross-system integrations and automations; champion AI-first GTM workflows and agents; document system configurations and integration architecture; partner with RevOps leadership and GTM stakeholders to translate requirements into scalable technical solutions.

Manage multi-state regulatory compliance and licensing for a transportation network company; lead legislative and policy engagement; oversee a small litigation portfolio including labor and civil claims; advise cross-functional teams on AI, data use, and contract/regulatory implications; draft filings, respond to investigations, and build AI-enabled compliance workflows.

Own retention, expansion, and account health for a Tier 1 book, driving strategic district-level growth through in-person engagement, Challenger-led selling, cross-functional execution, pricing negotiations, and AI-enabled operational reporting and insights.

Manage ongoing client operations and issue resolution as primary contact for assigned clients. Lead implementations from contract to launch, analyze ride data to improve service, collaborate cross-functionally to solve systemic issues, partner with support to resolve real-time incidents, run business reviews, and drive adoption and service optimization to deliver exceptional client experiences.

Lead a pod of 5-6 BDMs and CarePartner Specialists to manage onboarding, integration, and performance of professional WAV and Livery fleets. Drive supply-side performance, standardize operational SOPs, manage high-complexity partnerships, escalate operational issues, coach and develop team members, and align supply acquisition with district demand and operational capacity.

The Regional Account Manager is accountable for managing client relationships, driving account strategy, and ensuring retention and expansion of revenue through client engagement and cross-functional collaboration.

Manage contract review processes, draft agreements, maintain templates, oversee legal operations, and utilize AI tools for efficiency in a fast-paced legal environment.

Manage compliance analysis, support school districts on regulatory issues, oversee Ironclad platform, handle contract data, and lead legal operations.

The VP of Engineering will lead the engineering organization, scale operations, drive AI integration, ensure delivery excellence, and foster collaboration with product and technology teams.

As a Sales Development Representative, you'll build relationships with school districts, educate them on our services, and qualify leads for Account Executives while meeting sales quotas.

The Senior Product Manager will lead AI-driven product strategies, enhance customer experience, and manage complex enterprise systems, focusing on user-centric design and data-driven decisions.

Sell HopSkipDrive to net-new K-12 and public-sector partners by sourcing and closing deals, building pipeline, applying MEDDPICC qualification, engaging multiple stakeholders, traveling up to 50%, and using AI and CRM tools to maintain forecast and drive revenue growth.