Strategic Account Executive

About the role

You will own the end to end sales cycle for new business within the strategic account segment, driving revenue growth and long term partnerships. You will challenge the status quo by leading every conversation with insight rather than a standard pitch, teaching prospects about mobility solutions they have not previously considered. You will take ownership of multi threaded engagement across buying committees, mapping stakeholder dynamics and building consensus toward decisive action. You will always be closing by negotiating terms, converting initial contracts into paying clients, and expanding those accounts during the early onboarding phase. You will build and maintain a robust pipeline, sourcing a meaningful portion of your own opportunities while collaborating closely with our SDR organization. You will demonstrate deep curiosity and compassion by uncovering unspoken concerns, political dynamics, and the true decision making structure behind every sale. You will partner cross functionally with Support, Product, Trust and Safety, and Operations to implement client feedback and refine our offerings in the market.

Key facts

What you'll do

Define and own a compelling value proposition for net new prospective business partners, articulating the HopSkipDrive story in a way that connects directly to their specific transportation challenges.

Conduct discovery driven conversations that uncover latent needs, budget authority, and the economic buyer within complex school district and government agency environments.

Apply MEDDPICC qualification rigor to every opportunity, ensuring early identification of the true economic buyer and maintaining accurate forecast discipline across the pipeline.

Build and multithread relationships across multiple stakeholders including transportation directors, operations leads, finance teams, and executive leadership simultaneously.

Map the full decision making structure for each target account, identify internal champions, and align organizational priorities toward a closed deal.

Leverage AI tools and modern sales methodologies to challenge the status quo, teaching prospects new perspectives and creating urgency for change.

Own the entire sales cycle from initial outreach through contract execution, ensuring a smooth transition for new clients during onboarding and early adoption.

Collaborate cross functionally with Support, Product, Trust and Safety, and Operations to implement client feedback and continuously refine our marketplace solutions.

Develop and manage a robust pipeline of opportunities, sourcing a significant portion of your own leads while working alongside our SDR team.

Demonstrate consistent ownership of key performance metrics, forecasting accuracy, and pipeline health to drive predictable revenue growth.

Champion the HopSkipDrive mission of creating mobility opportunity for all by enabling safe, fast, and simple supplemental student transportation at scale.

Adapt your communication style to resonate with different stakeholders, from operations teams to executive sponsors, always tailoring the message to their priorities.

Take control of the sales process by establishing clear timelines, decision criteria, and success metrics that move deals efficiently toward closure.

Act as a trusted advisor to school districts and government agencies, positioning HopSkipDrive as a partner rather than just a vendor in their transportation ecosystem.

Requirements

You must have a proven track record of selling into complex enterprise environments, including school districts and government agencies.

You must be comfortable operating in a fast growth, mission driven environment where AI is deeply embedded in how work gets done.

You must have the ability to multi thread complex sales efforts across multiple stakeholders and decision makers simultaneously.

You must demonstrate strong negotiation and closing skills, with experience in defining terms and converting opportunities into paying clients.

You must be able to qualify opportunities using a structured methodology such as MEDDPICC and maintain accurate forecasting discipline.

You must have excellent communication skills, both written and verbal, with the ability to tailor messaging for diverse audiences.

You must be highly adaptable and capable of learning new tools and sales approaches quickly in a rapidly evolving technology landscape.

You must be passionate about creating meaningful impact in the mobility and education sectors, aligning your work with HopSkipDrive's mission.

You must be able to work fully remotely from anywhere in the USA, managing your own schedule while meeting agreed upon performance targets.

Practical notes

LENGTH: 700-900 words. No HTML, no markdown, no em dashes.