HopSkipDrive

• 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.

• 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.

• 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.

• 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.

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're an AI-forward company, and we expect every person on our team to be too. We use AI tools to do our best work — drafting, analyzing, building, and shipping faster than we could without them — and we invest in training, share what works, and govern AI use thoughtfully. We don't expect you to be an expert when you start. We do expect you to be curious, willing to learn, and ready to use the best tools available to move our mission forward. We're remote-first, mission-driven, and built for people who want to do work that matters with people who hold a high bar. Who We Are We are a driven, mission-focused team, passionate about transforming transportation through innovation and impact. Rather than just selling a service, we build lasting partnerships with school districts and government agencies, solving their toughest challenges with our vetted CareDriver marketplace and cutting-edge solutions. As a Revenue team, our goal is clear: drive revenue growth, deliver value to our clients, and redefine what’s possible in mobility — while making a meaningful difference for those who need it most. The Role The Regional Account Manager (RAM) is responsible for day-to-day account management and long-term account strategy across a Tier 2 book of business. This role owns retention, expansion, and overall account health while serving as the strategic quarterback for complex districts. With support from Regional Sales Management, the RAM sets and executes account strategy and provides recommendations to senior staff for required resources, collaborates cross-functionally with Metro Service Managers to drive operational excellence at the account level and plays an active role in identifying product-level gaps and strategies for product penetration by account. This is a revenue-owning role focused on driving measurable outcomes through strategic account planning, Challenger-led selling, and cross-functional execution. Success requires strong client communication skills, demonstrated commercial acumen, high operational rigor and the ability to proactively coordinate and align both internal cross-functional partners and senior external stakeholders. To excel in this role, you will be expected to take ownership of and demonstrate the following key job responsibilities: - In-Person Client Engagement: Dedicate 2-3 days each week to on-site client visits to foster relationships, deepen understanding of client needs, and drive meaningful engagement. Additional national travel may be needed and reliable transportation is required. - Spearhead Enterprise Growth: 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. - Manage Client Accounts: Deliver exceptional client service, build and maintain strong, multi-threaded relationships across operational, technical, and executive stakeholders. - Seek Net-New Opportunities: 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 Tailored Value: Communicate confidently with client executives, influencing decision-making through data, insight, and outcome-based recommendations. - Partner Cross-Functionally: Align Sales, Operations, Product, Finance, Trust & Safety and Support around client priorities and optimize our offerings to their needs. - Lead Pricing Discussions: Lead renewals and expansions, including structured negotiations and closing motions. Who You Are Required - 5+ years of experience in Account Management, Customer Success, or Consultative Sales in SaaS, marketplace, logistics, or services environments. - Proven ownership of retention and expansion revenue. - Strong executive communication and presentation skills. - Demonstrated success managing complex, multi-stakeholder accounts. - Advanced CRM discipline and data fluency (Salesforce or equivalent). - Experience leading cross-functional account execution. - Comfort operating in ambiguity with accountability for outcomes. Preferred - Experience in education, government, or regulated markets. - Familiarity with Challenger or similar insight-led sales methodologies. - Background in transportation, logistics, or marketplace platforms. 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, VC-backed company in a hugely attractive space with significant upside potential. HopSkipDrive is committed to fair and equitable compensation practices. The salary range for this role is an $85,000-90,000 base with an OTE of $130,000 - $140,000. This position is remote and, as such, compensation will ultimately be in line with the location in which the position is filled. Final compensation for this role will be determined by several factors such as a candidate’s relevant work experience, skill set, certifications, and specific work location. The total compensation package for this role 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. NOTE* This role will be remote but candidates must be based in the Los Angeles, CA area. There will be travel required. The role will require 2-3 days on-site client visits every week.

Role Description We're looking for a Strategic Talent Lead who operates as a strategic partner, a process architect, and an AI-powered change agent, all at once. This is not just a fill-the-req role. - Own the transformation of how HopSkipDrive identifies, attracts, and hires top talent. - Rethink our processes from the ground up — cutting manual work, embedding AI tools, and building a recruiting experience that reflects our innovative company. - Be the trusted partner for hiring managers to build their teams. - Lead with data and think in systems. - Transform the talent function, seeing process gaps as design opportunities. - Use AI tools as a matter of course, holding a high bar for candidate and hiring manager experience. - Bring intellectual curiosity, critical thinking, and a strong point of view. - Present recommendations to leadership, coach hiring managers, and dig into ATS audits. Qualifications - 6+ years of talent acquisition experience in fast-paced tech environments. - Proven track record of managing full-cycle recruiting across the organization. - Experience recruiting for GTM roles is required. - An AI-native builder mindset: ship automations and design intelligent workflows. - Expertise in running high-velocity, outbound-heavy operations. - A systems-thinking approach, balancing speed and scale with quality. - Proven ability to operate as a strategic partner to leadership. - A deep interest in AI research and the broader technology ecosystem. Requirements - Drive Talent Strategy & Pipeline - Own full-cycle recruiting across functions from intake through close. - Build and execute strategic, customized sourcing strategies. - Serve as a trusted advisor to hiring managers and senior leaders. - Manage and optimize our use of Greenhouse (ATS). - Own the recruiting tech ecosystem. - Lead AI-Forward Process Transformation - Audit current recruiting workflows and identify areas for improvement. - Embed AI into day-to-day recruiting operations. - Build a repeatable process for staying current on recruiting technology. - Elevate Stakeholder Experience & Internal Partnership - Deliver a white-glove experience for hiring teams. - Present recruiting data and insights to senior leaders. - Coach hiring managers on effective interviewing practices. - Own Data, Insights & Continuous Improvement - Build and maintain recruiting dashboards. - Use data to drive decisions and make evidence-based recommendations. - Champion a culture of continuous improvement. Benefits - Equity for every full-time employee. - Flexible vacation. - Medical, dental, vision, and life insurance. - 401(k) and FSA. - Opportunity to work for a VC-backed company with significant upside potential.

• Negotiate terms and close new business • Source 20-30% of own pipeline • Engage with multiple stakeholders in decision-making process • Utilize AI tools for productivity • Maintain Salesforce discipline

• Administer and continuously optimize Salesforce — owning user management, custom objects, flows, validation rules, permission sets, and reporting dashboards to ensure it operates as a reliable single source of truth • Own the GTM tool stack end-to-end: maintain a live inventory of all tools, manage vendor relationships, track contract renewal timelines, and provide data-driven recommendations on consolidation, expansion, or replacement • Design and deploy new tool workflows and cross-system integrations that eliminate manual handoffs and increase velocity across Sales, Marketing, and Customer Success • Champion an AI-first approach to GTM operations — proactively identifying opportunities to leverage LLMs, automation agents, and intelligent enrichment pipelines to reduce manual effort and surface actionable signal for revenue teams • Build and maintain integrations across the GTM stack (e.g., Salesforce, ZoomInfo, Outreach, Gong, Spiff, Omni) via APIs, MCPs, native connectors, or iPaaS platforms to create a high-fidelity, connected data ecosystem • Document system configurations, workflow logic, and integration architecture to ensure operational continuity and enable self-service for end users and business stakeholders and also enable AI automations and agents. Document first and use that context layer to build. • Partner with RevOps leadership and GTM stakeholders to translate business requirements into scalable technical solutions, proactively flagging risks and surfacing opportunities before they become problems • You’ll report directly to the Director of Revenue Operations and work closely with senior team members and cross-functional GTM leaders.

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 20 states. 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're an AI-forward company, and we expect every person on our team to be too. We use AI tools to do our best work — drafting, analyzing, building, and shipping faster than we could without them — and we invest in training, share what works, and govern AI use thoughtfully. We don't expect you to be an expert when you start. We do expect you to be curious, willing to learn, and ready to use the best tools available to move our mission forward. We're remote-first, mission-driven, and built for people who want to do work that matters with people who hold a high bar. Who We Are This role will provide exceptional, proactive support for our clients throughout the operational lifecycle. This position bridges the gap between Implementation, Customer Success, and ongoing Operations to streamline service delivery and ensure a premium client experience. The Metro Service Manager will take ownership of ongoing client operations and issue resolution. This new role will work closely with cross-functional teams to proactively address client needs, improve service quality, and optimize ride experiences. We are looking for creative problem-solvers who, like us, believe that challenges require innovative approaches, unique perspectives, and new ways of thinking. - 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. Who You Are You’re a proactive and strategic customer success professional who excels at building strong client relationships, solving complex challenges, and driving measurable results. You thrive in fast-paced environments and are passionate about enhancing client experiences through data-driven insights and collaboration. - 5+ years of experience in Customer Success, Account Management, or Implementation roles, preferably in a high-pressure or start-up environment. - Willingness to travel (10%-20%) to strengthen client relationships and support service strategies. - Proven ability to manage client relationships, resolve issues swiftly, and deliver exceptional customer service. - Strong communication skills, both written and verbal, with the ability to present insights and solutions effectively in meetings and reports. - Expertise in analyzing data, identifying trends, and implementing actionable solutions to improve client outcomes. - Experience collaborating across teams to address root causes of recurring challenges and enhance service delivery. - Proficiency with CRM tools such as Salesforce or Kustomer, and advanced Excel skills are preferred. - A proactive, problem-solving mindset with the initiative to drive continuous improvement and innovation. - You are tech-forward and committed to operational excellence. You actively leverage AI tools (such as Gemini) to streamline workflows, summarize complex client issues, refine communication, and derive insights from data sets, and you are eager to apply this expertise to enhance client outcomes 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, VC-backed company in a hugely attractive space with significant upside potential. HopSkipDrive is committed to fair and equitable compensation practices. The base salary range for this role is $80,000 - $90,000. This position is remote and, as such, compensation will ultimately be in line with the location in which the position is filled. Final compensation for this role will be determined by several factors such as a candidate’s relevant work experience, skill set, certifications, and specific work location. The total compensation package for this role 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. *NOTE* This role will be remote but candidates must be able to travel occasionally regionally (10-20%).

• 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.