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%).
Skills Required
- 5+ years of experience in Customer Success, Account Management, or Implementation roles
- Willingness to travel 10%-20%
- Proven ability to manage client relationships and resolve issues swiftly
- Strong written and verbal communication skills; ability to present insights and solutions effectively
- Expertise in analyzing data, identifying trends, and implementing actionable solutions
- Experience collaborating across teams to address root causes and enhance service delivery
- Experience leading and managing implementation from contract signed through launch
- Proficiency with CRM tools such as Salesforce or Kustomer
- Advanced Excel skills
- Proactive, problem-solving mindset with initiative to drive continuous improvement and innovation
- Experience conducting virtual and in-person client meetings and driving business reviews
- Experience leveraging AI tools (such as Gemini) to streamline workflows and derive insights
What the Team is Saying
HopSkipDrive Compensation & Benefits Highlights
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Healthcare Strength — Corporate roles include medical, dental, vision, HSA/FSA options, mental‑health resources/EAP, and short‑ and long‑term disability. Paid parental leave is explicitly included within the health and wellbeing offering.
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Leave & Time Off Breadth — Employees are offered flexible or generous PTO, paid holidays, and a company‑wide end‑of‑year closure, with sick time also available for employees and families. Feedback suggests the remote‑first setup further supports time away when needed.
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Equity Value & Accessibility — Equity is provided to full‑time employees and positioned as a standard part of compensation. Feedback suggests this ownership component meaningfully augments total rewards for corporate roles.
HopSkipDrive Insights
What We Do
We help get students to their destinations, safely and on time. Our technology connects school partners to a network of highly vetted drivers with small vehicles and wheelchair-accessible vehicles, complementing the yellow bus, filling in gaps, and enabling schools to support student transportation needs. Our partnerships with school districts, child welfare agencies and nonprofits ensure equitable educational access for our most vulnerable populations, including youth in foster care, youth experiencing homelessness, and youth with special needs.
Why Work With Us
HopSkipDrive exists to create opportunity for all through mobility. As the leader in innovative, supplemental school transportation, we’re taking a different approach to addressing inequities in educational access that are affecting millions of kids each day. We’re paving the way for a future where every student has the chance to succeed.
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HopSkipDrive Offices
Remote Workspace
Employees work remotely.
HopSkipDrive’s headquarters is located in Los Angeles’ Little Tokyo district and we love this space! However we believe strongly that most roles allow for a remote-first approach to work, and most of our employees work remotely.
