HopSkipDrive

Marketing

• 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.

Vice President, Marketing

General Counsel

• Own multi-state regulatory compliance obligations for HopSkipDrive as a transportation network company operating in the education sector, including TNC licensing, driver qualification standards, DMV record check requirements, and state-specific transportation regulations.
• Draft and submit regulatory filings, advice letters, and compliance attestations to state agencies; track and manage agency review, approval, and disposition.
• Advise on revenue contract and RFP provisions with regulatory implications, including background check requirements, reporting obligations, and driver and vehicle standards.
• Advise internal stakeholders on regulatory requirements for new market entry and ongoing compliance obligations in existing markets.
• Build AI projects and workflows related to regulatory matters.
• Monitor and analyze federal and state legislation affecting HopSkipDrive’s operations, with a focus on transportation network companies, school pupil transportation, and automated decision systems.
• Develop legal and policy positions on pending legislation; collaborate with the Policy and Government Relations teams to prepare bill analyses, public comments, and engagement strategies.
• Assist with bill review and bill drafting in partnership with the Policy team.
• Identify legislative trends and develop proactive compliance strategies, particularly around TNC regulation, school transportation, and gig economy classification.
• Represent HopSkipDrive’s interests in regulatory rulemakings before state public utility commissions and transportation agencies.
• Monitor and manage responses to public records and disclosure requests from state and local agencies.
• Leverage AI tools for more efficient legislative analysis.
• Oversee a book of claims related to labor and employment claims.
• Manage a small number of cases or claims related to civil litigation including discovery strategy, preparing corporate witnesses, and directing litigation defense.
• Support outside counsel in preparing for and conducting arbitrations.
• Handle subpoenas, service of process, and regulatory investigations, coordinating with outside counsel as appropriate.
• Build AI projects and workflows related to litigation.
• Manage data use agreements and research partnerships with academic institutions and government agencies.
• Provide legal research and rulemaking assistance as needed to support a busy and growing regulatory portfolio.
• Serve as a legal subject matter expert on AI and automated decision-making, advising on compliance with emerging state AI legislation and internal AI governance frameworks.

Senior Counsel – Policy & Regulatory

Account Manager

• Unify the Account Management Lifecycle: Lead a specialized pod of 5–6 direct reports (BDMs and Specialists), ensuring that professional fleets are not just contracted, but successfully integrated and optimized for daily ride volume.
• Drive Professional Supply Performance: Own supply-side performance for the WAV and Livery categories, ensuring we have the professional density required to meet district demand.
• People Leadership & Development: Manage and coach a team of individual contributors. You will be responsible for their career growth, performance management, and daily tactical guidance.
• Standardize Operational Blueprints: Eliminate "islands of process" by enforcing strict documentation standards. You will ensure every market launch and CarePartner relationship follows a consistent process.
• Manage High-Complexity Portfolios: As a player-coach, you will directly manage a select group of high-complexity strategic partnerships, modeling excellence in account management for your team.
• Act as the First Point of Escalation: Serve as the primary operational lead for complex CarePartner negotiations or significant service-level gaps within your pod.
• Optimize the "Hunter/Farmer" Handshake: Partner with Revenue and Sales Ops to ensure that new supply acquisition is perfectly aligned with upcoming district demand and operational capacity.

Pod Lead, Specialty Account Management

AI Engineer

• Build and maintain shared infrastructure: secure web app hosting infrastructure, MCP/API standards, secret/key management, model selection, guardrails, and a centralized pattern library that all builders across the organization can pull from.
• Own the review, tracking, and advisory process for all corporate AI and automation builds — MCP servers and tool configurations, Claude Skills, API integrations, and agentic workflows — before deployment.
• Partner directly with AI specialists across departments to identify, scope, and build AI and automation solutions that meet high standards for cost, security, and scalability security before they ship.
• Define and maintain the secure intake path for AI and automation requests across the organization, replacing ad-hoc builds and shadow IT with a governed, cost-effective, and scalable process.
• Contribute to the organization’s AI cost efficiency by monitoring, alerting, and setting thresholds on AI spend across usage-based tools and platforms.

AI & Automations Lead

• Dedicate 2-3 days each week to on-site client visits to foster relationships, deepen understanding of client needs, and drive meaningful engagement.
• Drive strategic expansion across HopSkipDrive’s product suite through structured discovery and Challenger methodology. Build and execute district-level growth strategies, including multi-threaded stakeholder plans while owning retention, expansion, and overall performance of named accounts.
• Deliver exceptional client service, build and maintain strong, multi-threaded relationships across operational, technical, and executive stakeholders.
• Lead multi-department discovery within districts to uncover unmet needs and quantify opportunity. Drive strategic expansion across HopSkipDrive’s product suite through structured discovery and Challenger methodology.
• Communicate confidently with client executives, influencing decision-making through data, insight, and outcome-based recommendations.
• Align Sales, Operations, Product, Finance, Trust & Safety and Support around client priorities and optimize our offerings to their needs.
• Lead renewals and expansions, including structured negotiations and closing motions.
• Utilize AI to craft personalized meeting agendas, synthesize complex stakeholder needs, and draft high-impact follow-up communications. Leverage AI to generate automated summaries of Salesforce (SFDC) data, transforming raw metrics into actionable, insight-led recommendations for executive stakeholders. Employ AI to assist in building recurring account reports, identifying product-level gaps, and creating scalable growth strategies that prioritize client outcomes by automating routine reporting and documentation, you will minimize administrative overhead, dedicating more time to discovery and deepening multi-threaded district relationships.

Regional Account Manager

• Dedicate 2-3 days each week to on-site client visits to foster relationships, deepen understanding of client needs, and drive meaningful engagement.
• Drive strategic expansion across HopSkipDrive’s product suite through structured discovery and Challenger methodology.
• Build and execute district-level growth strategies, including multi-threaded stakeholder plans while owning retention, expansion, and overall performance of named accounts.
• Deliver exceptional client service, build and maintain strong, multi-threaded relationships across operational, technical, and executive stakeholders.
• Lead multi-department discovery within districts to uncover unmet needs and quantify opportunity.
• Communicate confidently with client executives, influencing decision-making through data, insight, and outcome-based recommendations.
• Align Sales, Operations, Product, Finance, Trust & Safety and Support around client priorities and optimize our offerings to their needs.
• Lead renewals and expansions, including structured negotiations and closing motions.
• Utilize AI to craft personalized meeting agendas, synthesize complex stakeholder needs, and draft high-impact follow-up communications.

Senior Regional Account Manager

Manager

• Serve as the primary point of contact for assigned clients, ensuring needs are addressed and solutions delivered with urgency and professionalism.
• Respond to and resolve complex client inquiries, leveraging internal resources and collaboration to provide swift resolutions.
• Lead and manage the implementation of new business from contract signed through launch, ensuring a successful implementation process and maintaining communication with clients throughout the implementation.
• Act as a trusted advisor by continuously learning about HopSkipDrive's evolving products and services to best support clients.
• Gather and analyze feedback on ride experiences to identify improvement opportunities and implement service enhancements.
• Collaborate with cross-functional teams to address systemic issues affecting client satisfaction and advocate for impactful changes.
• Partner with Customer Support Specialists to resolve real-time ride and account issues while delivering weekly optimization reports.
• Conduct virtual and in-person client meetings to strengthen relationships, align on goals, and ensure adoption of best practices.
• Drive the strategic planning and execution of business reviews to align ongoing service strategies with client objectives.

Metro Service Manager

Software Engineer

• Lead and scale a high-performing engineering organization by building deep trust, diagnosing organizational strengths, and establishing the career growth paths and structural changes required to elevate performance.
• Engage deeply and credibly in system design and architecture discussions, helping senior engineers navigate complex technical trade-offs across our platform (Ruby on Rails, React, iOS/Android), service boundaries, and modern infrastructure investments.
• Pioneer the integration of AI and agentic capabilities into our software development lifecycle, spanning the evaluation of new technical infrastructure, coaching teams through change management, and establishing the workflows, testing methodologies, and QA guardrails required to safely accelerate shipping velocity.
• Own the Engineering department's delivery and operational excellence, ensuring predictable, high-quality execution, world-class reliability, and continuous improvement of technical health and process discipline.
• Partner closely with the CPTO, SVP of Product, Design, Data, and Operations to align product vision with technical strategy and drive unified customer and business outcomes.
• Manage the engineering department's fiscal health, including headcount, contractors, software, and infrastructure budgets.

VP, Engineering

Sales Development Rep

• Create the first stage relationships with prospects at school districts
• Educate prospects on HopSkipDrive’s service
• Schedule meetings for prospects to speak with Account Executives
• Research and evaluate prospective leads
• Establish a rapport with potential prospects
• Use a consultative sales approach during outreach
• Cold call and email identified leads
• Use Salesforce CRM to manage sales funnel
• Meet or exceed SDR quotas
• Qualify leads that express interest in HSD’s service
• Meet or exceed assigned monthly and quarterly goals