Pod Lead, Specialty Account Management

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:

The Specialty Transportation team is the strategic engine behind HopSkipDrive's most complex, mission-critical services. This role leads the Professional Supply Pod, bringing together Business Development Managers and CarePartner Specialists into a single, high-performance unit focused on our professional WAV and Livery fleets.

The Role: As the Manager, ST Account Management, you are a strategic player-coach responsible for the end-to-end health of our professional supply portfolio. You will manage a team of multi-level professionals, bridging the gap between high-level supply contracting and daily operational fulfillment. You are responsible for ensuring that the "handshake" between sales and execution is flawless, documented, and scalable. This role reports to the General Manager, Specialty Transportation and is a critical leadership layer designed to drive consistency across our most complex markets.

You will be responsible for the following:

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.

Who You Are: You are a seasoned manager who thrives on building systems, developing talent, and leveraging modern tools to scale operations. You understand that scaling a specialized business requires moving away from individualized "heroics" and toward repeatable, documented processes. You bring:

Proven People Management: 5+ years of experience managing professional teams, including a track record of developing and promoting mid-level individual contributors.

Systems-Thinking & Rigor: You are obsessed with documentation and "playbooking." You have a proven ability to take complex, manual processes and turn them into scalable SOPs.

AI & Automation Tech-Fluency: You actively leverage AI and automation tools (e.g., LLMs for drafting documentation, workflow automation, or data synthesis) to accelerate team productivity, streamline communication, and eliminate repetitive tasks. You encourage your team to use AI responsibly to work smarter.

Player-Coach Mentality: You enjoy being "in the weeds" of a complex negotiation or operational challenge while maintaining the bird’s-eye view required to lead a department.

Collaborative Diplomat: You can fluidly navigate the natural friction between supply acquisition and operational fulfillment, finding the "win-win" for the business, the team, and the client.

Data-Driven Operator: You use supply-side metrics to drive team performance. You are comfortable using data tools to identify gaps and forecast supply needs.

Comfort with Ambiguity & Change: You thrive in a fast-paced, evolving marketplace environment. You can chart a clear path forward for your team even when operational blueprints are still being written.

Senior Stakeholder Presence: You have the gravitas and communication skills to represent the Specialty Transportation division in cross-functional leadership meetings and strategic planning sessions.

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, PA **