HopSkipDrive

Manage end-to-end marketplace performance by designing predictive models and optimizing supply-demand matching while leading cross-functional projects. | 3+ years analytical or operations experience, proficiency in Excel, SQL, AI tools, stakeholder management, and scalable process building. | At HopSkipDrive, our goal is to create opportunity for all through mobility. We’re a technology company that solves complex transportation challenges where there is a heightened need for safety, equity, and care. Through our marketplace, we connect kids, older adults, or anyone needing extra support to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts around 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 17 states around the country. We continue to expand at a rapid pace, making the Inc. 5000 list four times, as well as the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a Series D company and has raised $100M in funding to date. Who We Are The New Markets team is a fast-moving, high-impact group focused on launching and scaling operations in new regions. We are looking for an analytical, adaptable, and proactive operator to join our team and own the end-to-end success of our marketplace performance. Own near-term supply and demand forecasts for launch markets by designing and maintaining predictive models aligned to company directives. Operate and optimize marketplace configurations, including zip code mapping and cluster assignments, to maximize supply-demand matching efficiency. Design, build, and ship targeted productivity promotions to address fill rate gaps, manage market spend, and drive operational efficiency. Evaluate market health by monitoring net revenue and contribution margin, recommending cross-functional remediation for struggling markets. Monitor performance trends proactively, identifying root causes of off-track metrics and bringing forward data-backed recommendations. Own end-to-end project workstreams by defining scope, identifying owners, tracking progress, and ensuring cross-functional execution. Leverage AI-assisted workflows to accelerate research, monitor territory performance, and pressure-test strategic recommendations. Who You Are You are a high-agency operator who thrives in ambiguous environments and possesses a relentless drive to solve complex operational challenges. You have a proven track record of managing stakeholders, utilizing data to influence outcomes, and building scalable processes from the ground up. 3+ years of experience driving superior results in analytical, cross-functional, or operations roles, ideally in marketplace, logistics, or high-growth environments. Excel/Google Sheets power user capable of building complex, elegant models with advanced formulas and dashboards that work for non-technical stakeholders. Demonstrated ability to make nuanced business decisions based on imperfect information while remaining accountable for the outcomes. Proven ability to lead projects involving stakeholders who do not report to you, aligning teams and resolving friction to drive closure. Strong communication skills with the ability to translate complexity for different functions and levels without losing precision. High agency in identifying necessary actions and executing them independently in a fast-moving environment. Experience independently pulling and structuring data, with comfort using SQL or other data querying tools. Working knowledge of Tableau; expected to grow in report-building and contribute to team dashboards Demonstrated comfort using AI tools (such as Claude, ChatGPT, Perplexity, or equivalent) as an integral part of your actual daily workflow. You’ll flex across the full lifecycle of a launch — from infrastructure setup to cross-functional coordination to performance monitoring — doing whatever it takes to get a city operational and on a path to contribution margin positive. This is not a role for people who wait for direction. It’s for operators who identify gaps, build the tools to close them, and hold themselves accountable to 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 proud to operate as a drug-free workplace. HopSkipDrive is also committed to fair and equitable compensation practices. The salary range for this role is 95,000 - 110,000. 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. **This role will be fully remote in one of the following states AZ, CA, CO, DC, FL, GA, IL, IN, KS, MA, MD, MI, MN, MO, NC, NJ, NM, NV, NY, OK, OR, SC, TN, TX, UT, VA, WA, WI** Prioritizing candidates in Eastern and Southeast states based on business needs.

Translate business requests into rigorous analysis using AI tools and build cross-functional relationships to align on business objectives. | Requires 5+ years in data-intensive analyst roles within Sales or Revenue Operations with strong SQL, Excel/Google Sheets, cloud data warehouse, and BI tool expertise. | At HopSkipDrive, our goal is to create opportunity for all through mobility. We’re a technology company that solves complex transportation challenges where there is a heightened need for safety, equity, and care. Through our marketplace, we connect kids, older adults, or anyone needing extra support to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts around 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 17 states around the country. We continue to expand at a rapid pace, making the Inc. 5000 list four times, as well as the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a Series D company and has raised $100M in funding to date. Who You Are You are a proactive, technically-grounded analyst who moves fast and understands the intricacies of the sales motion and revenue operations. You are inherently curious and think critically about the details and the big picture. You are an expert at interpreting business requests and translating them into rigorous, reproducible analysis while utilizing AI tools to enhance your workflow. You excel at building strong cross-functional relationships to drive alignment on key business objectives. You have excellent communication skills and can translate findings for both technical and non-technical audiences. Requirements: 5+ years of experience in a data-intensive analyst role at a technology company, specifically within Sales or Revenue Operations. Strong SQL skills with the ability to build reliable models and debug complex data issues independently. Proven expertise building sophisticated, dynamic models in Excel or Google Sheets for scenario planning and revenue forecasting. Direct experience working within a cloud data warehouse like Snowflake. Technical proficiency with Salesforce CRM data models, reporting structures, and data hygiene practices. Demonstrated experience using modern BI tools (such as Tableau, Looker, or Omni) to build reports and self-serve analytics. Experience integrating AI systems like Claude into your analytical workflow to increase speed and accuracy. Nice to haves: Demonstrated ability to use GitHub for version control, documentation, and collaborative codebase creation. Demonstrated experience using scripting languages (R/Python) to generate reproducible analytic workflows. 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 proud to operate as a drug-free workplace. HopSkipDrive is also committed to fair and equitable compensation practices. The salary range for this role is $95,000 - $110,000. 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. This role will be fully remote in one of the following states AZ, CA, CO, DC, FL, GA, IL, IN, KS, MA, MD, MI, MN, MO, NC, NJ, NM, NV, NY, OK, OR, SC, TN, TX, UT, VA, WA, WI**

Manage inbound RFPs, maintain data tracking systems, provide data-driven insights, streamline processes, and collaborate across departments. | Detail-oriented with experience in RFP or sales operations, familiarity with Salesforce, strong organizational and data skills, and ability to manage multiple tasks efficiently. | At HopSkipDrive, our goal is to create opportunity for all through mobility. We’re a technology company that solves complex transportation challenges where there is a heightened need for safety, equity, and care. Through our marketplace, we connect kids, older adults, or anyone needing extra support to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts around 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 17 states around the country. We continue to expand at a rapid pace, making the Inc. 5000 list four times, as well as the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a Series D company and has raised $100M in funding to date. Who We Are: We are the RFP and Market Intelligence team, responsible for an impressive 30% of HopSkipDrive's revenue. We are the architects behind RFP-related business retention and expansion, expertly managing the RFP process and providing crucial sales support. We're looking for a detail oriented Request for Proposal (RFP) & Data Operations Analyst to join our team. In this role, you'll be the first line of defense for all inbound RFPs and a key driver in our response process. You will be responsible for vetting opportunities, setting up our tracking systems, tracking data in Salesforce, and providing crucial data that informs our outreach strategy. Manage inbound RFPs: Vet daily inbound RFPs from platforms like GovSpend, RFP Schoolwatch, and Starbridge, serving as the "first line of defense." Own data and systems: Manage the data tracking for all inbound activities, including the number of RFPs responded to and their sources. Maintain accurate records in Salesforce and our ticketing system (ClickUp/JIRA) to ensure tasks are organized and assigned correctly. Provide data-driven insights: Proactively track proposal data in Salesforce to inform outreach and planning efforts. Streamline processes: Establish and maintain tracking tools for each RFP, including Google Drive folders, Slack channels, and summary documents. Manage and submit Certificates of Insurance (COI) and Vendor forms. Collaborate effectively: Act as a team player, working with different departments to fulfill requests quickly and accurately. Who You Are: You are a highly organized and detail-oriented professional who thrives on creating order in a fast-paced, ever-changing environment. You have a knack for data and a passion for turning it into actionable insights. As a natural collaborator, you enjoy working with a variety of people and are known for your ability to fulfill requests quickly and efficiently. You're a proactive problem-solver who can manage multiple tasks with ease and a team player who is ready to jump in wherever needed. You are a highly organized and detail-oriented professional who thrives on creating order in a fast-paced environment. You have a knack for data and a passion for turning it into actionable insights. You are a natural collaborator who enjoys working with a variety of people and are known for your ability to fulfill requests quickly and efficiently. You're a proactive problem-solver who can manage multiple tasks with ease and a team player who is ready to jump in wherever needed. You have a background in a similar role, ideally with exposure to inbound RFP processes or sales operations. You are familiar with CRM software, preferably Salesforce. 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 proud to operate as a drug-free workplace. HopSkipDrive is also committed to fair and equitable compensation practices. The salary range for this role is between 70,000 - $80,000. 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. * This role will be fully remote in one of the following states AZ, CA, CO, DC, FL, GA, IL, IN, KS, MA, MD, MI, MN, MO, NC, NJ, NM, NV, NY, OK, OR, SC, TN, TX, UT, VA, WA, WI*

Provide exceptional client support across multiple channels, troubleshoot technical issues, process ride credits and refunds, manage alerts, and collaborate with teams to resolve customer problems. | Customer support experience with strong communication, technical aptitude, organizational skills, proficiency in CRM and support tools, and ability to work independently and collaboratively. | At HopSkipDrive, our goal is to create opportunity for all through mobility. We’re a technology company that solves complex transportation challenges where there is a heightened need for safety, equity, and care. Through our marketplace, we connect kids, older adults, or anyone needing extra support to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts around 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 17 states around the country. We continue to expand at a rapid pace, making the Inc. 5000 list four times, as well as the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a Series D company and has raised $100M in funding to date. Who We Are It is our mission to empower clients and caregivers by providing exceptional, empathetic support and efficient solutions that exceed expectations. We exist to set the standard for client support excellence, where every interaction embodies empathy, ownership, and a commitment to making tomorrow better for our clients! We do, and you will, support the business through the following responsibilities: Provide exceptional client support by resolving customer issues across multiple channels, including phone, email, and SMS. Offer technical support and troubleshooting assistance for the HopSkipDrive app and RideIQ platform. Process ride credits and refunds, ensuring accuracy and adherence to company policies. Answer questions and address concerns related to safety, ride scheduling, account management, and lost items, all while encouraging customer self-service. Manage pre-ride alerts, ensuring compliance with rider requirements. Gather and analyze client feedback to identify areas for improvement and enhance the overall user experience. Maintain a thorough understanding of HopSkipDrive's services, policies, and safety protocols. Collaborate with cross-functional teams to ensure comprehensive problem resolution for customers. Who You Are You're a compassionate problem-solver with a knack for turning frustrated clients into happy ones. With the following skills, you'll make a tangible and immediate impact on our team: Excellent communication and problem-solving skills, demonstrated through previous customer support experience. Strong organizational skills with the aptitude to prioritize and switch between different responsibilities seamlessly. Strong technical aptitude with the ability to troubleshoot platform and website issues. Excellent written and verbal communication skills, with the ability to convey information clearly and concisely. Customer-centric mindset with a genuine desire to help others and provide exceptional service. Proficiency in using support tools and software, including CRM systems and communication platforms. Ability to work independently and as part of a team, collaborating effectively with colleagues and cross-functional teams. Strong analytical and problem-solving skills, with the ability to identify trends and suggest improvements. 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 in Los Angeles, CA is $20 - $22. 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. * This role will be fully remote in one of the following states AZ, CA, CO, DC, FL, GA, IL, IN, KS, MA, MD, MI, MN, MO, NC, NJ, NM, NV, NY, OK, OR, SC, TN, TX, UT, VA, WA, WI*

Provide outstanding support to caregivers via phone and email, troubleshoot app issues, and collaborate with teams to ensure smooth rides. | Requires customer support experience, excellent communication skills, multitasking ability, proficiency in Google Workspace, and bilingual English-Spanish fluency preferred. | At HopSkipDrive, our goal is to create opportunity for all through mobility. We’re a technology company that solves complex transportation challenges where there is a heightened need for safety, equity, and care. Through our marketplace, we connect kids, older adults, or anyone needing extra support to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts around 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 17 states around the country. We continue to expand at a rapid pace, making the Inc. 5000 list four times, as well as the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a Series D company and has raised $100M in funding to date. Who We Are: Our Caregiver Support team is a vital part of ensuring every ride is delivered smoothly and safely. We're a dedicated group focused on providing exceptional support and with your help, we'll continue to build a community of highly engaged and satisfied caregivers: users of our platform who request and organize the trips of our riders, from school district transportation staff to parents and guardians. You will support the business through the following responsibilities: • Provide outstanding support to current and potential caregivers, prioritizing their engagement and satisfaction. • Achieve complete resolutions for caregiver inquiries and issues. • Collaborate cohesively with the broader Customer Support Operations Department teams to ensure a positive experience facilitate smooth and safe rides. • Build trust and comfort with caregivers through proactive problem-solving and excellent customer service. • Communicate effectively with caregivers via phone and email conduct call and messaging campaigns to customers as needed • Troubleshoot questions about our app and website, as well as recognize trends in issues and complaints to suggest changes to improve service. • Provide ride and account assistance to caregivers and their riders, consistent with HopSkipDrive policy and procedures. • Provide solutions that are complete and customer-focused. Complete projects and other support tasks as directed by support leadership Who You Are: You are calm under pressure and can be a beacon of comfort for caregivers both in high-stress situations and when answering questions. You are empathetic, outgoing, friendly, and have excellent people skills. With the following skills, you’ll make a tangible and immediate impact: • Fluent in written and verbal communications in both English and Spanish. • Prior experience in customer success, customer support, and/or call centers. • Demonstrated ability to multitask effectively while providing excellent customer service. • A knack for problem-solving: identifying, solving, and preventing problems before they arise. • Ability to respond to customer queries accurately and in a timely manner across various channels (phone, text, and email). • Proven track record of maintaining composure under pressure. • Ability to work collaboratively and effectively in a team setting. • Proficiency in Google Workspace is required, and proficiency with Kustomer is preferred. 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 proud to operate as a drug-free workplace. HopSkipDrive is also committed to fair and equitable compensation practices. The salary range for this role in Los Angeles, CA is $20.00 - $22.00. 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. • This role will be fully remote in one of the following states AZ, CA, CO, DC, FL, GA, IL, IN, KS, MA, MD, MI, MN, MO, NC, NJ, NM, NV, NY, OK, OR, SC, TN, TX, UT, VA, WA, WI**

As a Manager of Product Design, you will lead and mentor a team of product designers while driving design excellence across critical product areas. You will collaborate with cross-functional teams to ensure design efforts align with business objectives and user needs. | Candidates should have 7+ years of product design experience, including 2+ years in a leadership role. A strong portfolio demonstrating end-to-end product thinking and a deep understanding of user-centered design processes is essential. | At HopSkipDrive, our goal is to create opportunity for all through mobility. We’re a technology company that solves complex transportation challenges where there is a heightened need for safety, equity, and care. Through our marketplace, we connect kids, older adults, or anyone needing extra support to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts around 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 17 states around the country. We continue to expand at a rapid pace, making the Inc. 5000 list four times, as well as the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a Series D company and has raised $100M in funding to date. Who We Are Our Product Design team is at the forefront of crafting intuitive, impactful, and user-centered experiences that power our innovative marketplace and software solutions. We're passionate about high standards of design craft and accessibility, and we thrive on deep collaboration with our Product, Engineering, and Data teams. As we evolve, we're keenly focused on how AI integration will reshape user journeys, transparency, control, and trust within our emerging products. We're seeking a visionary design leader to help us elevate our team, guide exceptional design execution, and pioneer new levels of design excellence. Our work spans high-stakes enterprise tools, dynamic consumer mobile applications, and robust internal systems, all unified by our unwavering commitment to safety, empathy, and intelligent simplicity. As a Manager of Product Design, you'll be a pivotal leader, combining strategic vision with hands-on excellence. Specifically, you will: Lead & Mentor: Inspire, grow, and develop a high-performing team of product designers, fostering a collaborative, supportive, and growth-oriented culture. Drive Design Excellence: Provide clear guidance and constructive feedback, ensuring the delivery of high-quality, user-centered design solutions across critical product areas. Balance Leadership & Craft: Oversee day-to-day design execution while balancing hands-on design contributions with strategic team leadership and initiatives. Drive Cross-Functional Alignment: Collaborate closely with Product Management, Engineering, Data and stakeholders to ensure design efforts are deeply aligned with business objectives and user needs. Champion User Advocacy: Actively champion user-centered design principles, accessibility standards, and design best practices throughout the organization. Facilitate & Communicate: Lead design reviews, critiques, and presentations, effectively communicating design rationale and decisions to diverse stakeholders. Optimize & Innovate: Identify and implement opportunities to continuously improve design processes, tools, and team workflows, driving efficiency and fostering innovation. Measure Impact: Monitor and report on the impact of design initiatives, ensuring solutions are robustly informed by user research, data analytics, and continuous feedback loops. Shape AI-Powered Experiences: Guide the design of AI-powered features, demonstrating a strong intuition for leveraging automation while prioritizing human control, transparency, and trust. Who You Are You are a player-coach design leader who balances hands-on excellence with mentorship and strategy. You enjoy diving into the details within tools like Figma, but your true passion lies in developing others, connecting the dots across complex product ecosystems, and setting a consistently high standard for how design influences cross-functional collaboration. You are passionate about craft, not for its own sake, but because you know small details make big experiences. You bring a systems-thinking mindset, strong UX instincts, and a passion for translating complexity into clarity — especially in enterprise or B2B environments. 7+ years of product design experience, with 2+ years leading or managing designers. A strong portfolio that demonstrates end-to-end product thinking, craft, and impact across mobile and web platforms. Proven track record of delivering intuitive and elegant user experiences for web and mobile. Demonstrated success in building, mentoring, and scaling diverse, high-performing design teams, coupled with a genuine growth mindset and a desire to elevate others through constructive feedback, coaching, and shared critique. Deep expertise in user-centered design processes, usability best practices, and accessibility standards. A strong ability to leverage data and research—not just for validation, but to uncover hidden user needs, shape strategic direction, and tell compelling stories that drive superior product decisions. Hands-on experience designing AI-powered features, with a sophisticated understanding of when to embrace automation and when to ensure human oversight. Exceptional communication and storytelling skills, with the ability to influence and align stakeholders at all levels of the organization. A collaborative spirit, eager to partner closely with product managers, engineers, and stakeholders to define product strategy and deliver impactful solutions. Proficiency with modern design and prototyping tools (e.g., Figma), along with a solid understanding and experience with design systems and scalable design practices. Ability to balance strategic vision with hands-on execution in a fast-paced, growth-oriented environment. 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 $160,000 - $185,000. 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. * This role will be fully remote in one of the following states AZ, CA, CO, DC, FL, GA, IL, IN, KS, MA, MD, MI, MN, MO, NC, NJ, NM, NV, NY, OK, OR, SC, TN, TX, UT, VA, WA, WI**