--- title: 'Sr. Product Designer at HopSkipDrive' canonical: 'https://feeny.ai/job/sr-product-designer-hopskipdrive-remote-17s72qhj3yxk' type: 'job' last_seen: '2026-09-08' --- # Sr. Product Designer at HopSkipDrive - **Company:** HopSkipDrive - **Location:** Remote - **Work type:** remote - **Posted:** 2026-09-04 - **Last confirmed live:** 2026-09-08 - **Apply:** https://job-boards.greenhouse.io/hopskipdrive/jobs/6178390004 ## Job description ## 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 use AI every day, and not as a productivity add-on. It's woven into how we work at every level. We're rethinking how work gets done, who does what, and what a small team can accomplish. If you've already built AI into how you work, you'll hit the ground running. If you haven't, you'll need to be ready to learn fast and work differently than you have before. ## 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 Senior Product Designer to lead complex, high-visibility design initiatives, raise the bar on design craft, and help 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 Senior Product Designer, you will take the lead on complex design projects that significantly impact HopSkipDrive's usability and visual appeal. You will create end-to-end design solutions, from conceptual exploration to detailed interaction design, while advocating for user needs throughout the development process. You are expected to provide mentorship to junior designers and leverage user feedback and data to make informed design decisions that align with business goals. You'll: - Lead Strategic Design Initiatives: Contribute to product design vision and strategy, applying systems thinking to complex challenges and leading design initiatives that address strategic product opportunities across HopSkipDrive's portfolio. - Define Patterns & Consistency: Define UX patterns and ensure consistency across products, developing and implementing scalable design systems and components with strong proficiency in design tools, prototyping, and accessible design. - Drive Research-Informed Decisions: Conduct strategic design research to identify long-term opportunities, integrate user research and data analysis into strategic product decisions, and synthesize complex findings into clear, actionable insights. - Lead AI-Accelerated Discovery: Lead discovery phases using AI tools to synthesize research at a speed and depth not possible manually, bringing sharper, data-backed rationale into cross-functional design strategy conversations, and evaluating which design problems are strong candidates for AI-powered solutions. - Design AI-Powered Features: Design high-quality AI-powered product features with well-defined interaction patterns, error states, and edge cases — bringing a discerning eye to AI tool outputs and iterating with intent. - Mentor & Elevate the Team: Mentor other designers, facilitate design workshops and critiques, foster a collaborative design culture, and help establish team norms for effective, critical use of AI tools. - Communicate & Influence: Communicate and defend design rationale to executive stakeholders and cross-functional teams, facilitate cross-functional workshops to drive alignment, and present design strategy and vision to senior stakeholders. - Own Design Outcomes: Own design outcomes for significant product areas, define and measure success in terms of business and user metrics, and drive measurable customer impact through well-designed AI experiences — reducing friction, improving personalization, and increasing user confidence. ## Who You Are You are a design leader who blends advanced craft with strategic thinking and a passion for mentorship. You bring a systems-thinking mindset, strong UX instincts, and a track record of translating complexity into clarity — especially in enterprise or B2B environments. - 5+ years of product design experience, with a track record of leading complex, cross-functional design initiatives end to end. - Advanced UX/UI design skills with a focus on holistic user experiences, strong visual execution, and proficiency in end-to-end design. - Experience establishing and maintaining design standards, best practices, and scalable design systems for a team. - Proven ability to lead complex prototyping and usability testing efforts, ensuring high-quality, accessible results across multiple product areas. - Demonstrated ability to integrate user research and advanced data analysis into strategic product decisions, and to lead research initiatives that inform roadmap and strategy. - Experience in designing for mobile and web platforms - Experience mentoring designers, facilitating critiques and workshops, and fostering a collaborative, user-centered design culture. - Exceptional communication skills, with the ability to defend design rationale to executive stakeholders and build strong relationships across the organization. - Hands-on experience using AI tools to accelerate discovery, research synthesis, and prototyping — with the judgment to know when AI interpretation is reliable and when human judgment must lead. - A discerning eye for AI-generated design output, consistently iterating with intent and creating new skills or workflows to increase team efficiency and consistency. - Proficiency with modern design and prototyping tools (e.g., Figma), along with solid understanding of design systems and scalable design practices. 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 $135,000 - $163,000. 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, CT, DC, FL, GA, IL, IN, KS, MA, MD, MI, MN, MO, NC, NJ, NM, NV, NY, OH, OK, OR, SC, TN, TX, UT, VA, WA, WI** ## About HopSkipDrive ## Company Overview - **One-liner**: HopSkipDrive is a technology company that provides safe, supplemental transportation solutions for students, older adults, and anyone needing extra support, primarily partnering with school districts. - **Entity Type**: Private (Series D) - **Headquarters**: Los Angeles, California, USA - **Founded**: 2014 - **Founders**: Joanna McFarland, Carolyn Yashari Becher, Janelle McGlothin ## Core Business - Primary industry/industries: Student Transportation, EdTech, Mobility - Target customers: B2B (K-12 school districts, government agencies, nonprofits) and B2C (families and caregivers) - Mission or purpose statement: "To create opportunity for all through mobility." ## Products & Services - **Supplemental School Transportation Platform**: A marketplace connecting students to highly vetted CareDrivers in small vehicles, filling gaps left by traditional yellow bus services. Supports general education, special needs (IEPs), McKinney-Vento (homeless), and foster care students. - **RouteWise AI™**: An AI-powered routing and scheduling software that creates customized, data-driven transportation plans tailored to school district requirements, priorities, and constraints. - **CareDriver Network**: A flexible network of vetted caregivers who provide rides using their own vehicles, enabling bookings with as little as six hours' notice. - **Safe Ride Technology**: A comprehensive safety suite including a 15-point CareDriver certification, real-time ride tracking, and industry-leading safety protocols. ## Market Standing - **Valuation/Market Cap**: Not publicly available (Series D, raised $100M in total funding) - **Key Metric**: Total Funding of $100M; has facilitated over 3.3 million rides and completed over 130 million safe miles. - **Notable Investors/Partners**: Partners with over 10,000 schools across 13+ states including California, Washington, Arizona, Colorado, Nevada, Texas, Wisconsin, Michigan, Pennsylvania, Virginia, Indiana, Tennessee, and Missouri. - **Growth Signals**: Honored as an Inc. 5000 company and Built In Best Places to Work. Recently recognized with an Honorable Mention in the Transportation category for RouteWise AI. Operates in over 13 states and continues to expand into new counties. ## Competitive Advantages - **Safety-First DNA**: Industry leader in safety with a 15-point CareDriver certification, cutting-edge Safe Ride Technology, and a relentless focus on continuous improvement. - **Niche Focus on Equity**: Directly addresses transportation inequities for vulnerable student populations (foster care, homeless, special needs) mandated by laws like ESSA and McKinney-Vento. - **Flexible, Tech-Enabled Solution**: AI-powered routing (RouteWise AI) and a flexible network of CareDrivers that can be deployed in as little as 6 hours, solving bus driver shortages and complex scheduling. - **Proven Scale and Trust**: Trusted by over 10,000 schools and has facilitated millions of rides, demonstrating a reliable and scalable model. ## Strategic Focus - **Expansion**: Continuously expanding into more states and counties across the US to serve more school districts and communities. - **Technology Leadership**: Investing in AI-powered tools like RouteWise AI to optimize routing, improve efficiency, and provide data-driven insights to partners. - **Deepening Impact**: Focusing on serving the most vulnerable student populations (special needs, foster care, homeless) and expanding services to older adults and government agencies. - **Scaling the CareDriver Network**: Recruiting and retaining a large, highly vetted network of CareDrivers to meet growing demand. ## Why Work Here - **Culture**: Mission-driven culture focused on "creating opportunity for all through mobility." Values include safety, equity, care, and making tomorrow better. - **Remote/Hybrid Policy**: Remote-first company. Employees are located across the US with physical hubs in Los Angeles (HQ), Denver, New York City, Houston, and Nashville. Most roles allow for a fully remote approach. - **Notable Perks & Benefits**: - Fully remote work option and flexible time off. - 11 annual paid holidays and a week-long closure at the end of the year. - Home internet reimbursement and professional development/learning stipend. - Comprehensive medical, dental, and vision insurance. - 401K plan with company ownership/equity. - Paid parental leave and short- & long-term disability insurance. - Employee referral bonuses and internal rewards/recognition program. - Remote & in-person quarterly team events and a social committee for connection. - **Engineering Culture**: Encourages the use of modern tools, including AI, to solve problems efficiently. Interview process includes a take-home assessment where candidates are actively encouraged to use AI tools and discuss their strategy. ## Sources 1. [hopskipdrive.com](https://www.hopskipdrive.com/) 2. [hopskipdrive.com/careers](https://www.hopskipdrive.com/careers/) 3. [hopskipdrive.com/about](https://www.hopskipdrive.com/about/) 4. [LinkedIn](https://www.linkedin.com/company/hopskipdrive) 5. [Greenhouse Job Board](http://job-boards.greenhouse.io/hopskipdrive) ## Other roles at HopSkipDrive - [Director, Commercial Law](https://feeny.ai/job/director-commercial-law-hopskipdrive-remote-22yq7nb6kqzg) - [VP, Marketing](https://feeny.ai/job/vp-marketing-hopskipdrive-remote-s3vpkzn9yp31) - [Sr Counsel - Policy & Regulatory](https://feeny.ai/job/sr-counsel-policy-regulatory-hopskipdrive-remote-1b2m4hrr9cja) - [Pod Lead, Specialty Account Management](https://feeny.ai/job/pod-lead-specialty-account-management-hopskipdrive-united-states-vwav1mw3hkxj) — United States - [Strategic Talent Lead](https://feeny.ai/job/strategic-talent-lead-hopskipdrive-remote-3kard1x8vfn4) - [Strategic Account Executive](https://feeny.ai/job/strategic-account-executive-hopskipdrive-united-states-be28j9jbaj9a) — United States - [GTM Engineer](https://feeny.ai/job/gtm-engineer-hopskipdrive-united-states-3epa3cjjkydz) — United States - [Metro Service Manager](https://feeny.ai/job/metro-service-manager-hopskipdrive-united-states-qyqyrcct9erz) — United States - [Sr. Regional Account Manager](https://feeny.ai/job/sr-regional-account-manager-hopskipdrive-united-states-wrb6hdtz2t8j) — United States - [Regional Account Manager](https://feeny.ai/job/regional-account-manager-hopskipdrive-united-states-8n75epnjbyd5) — United States