Metro Service Manager

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

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%).