[Hiring] Strategic Account Executive @HopSkipDrive

Role Description

As Strategic Account Executives, we provide value to net-new prospective business partners by:

• Telling the HopSkipDrive story.
• Connecting our unique value propositions to their needs.
• Creating urgency and closing deals to bring solutions to reality.
• Challenging the status quo and pushing prospects to innovate alongside us.

Key job responsibilities include:

• Always be Closing: Effectively negotiate terms, execute by closing new business, convert to a paying client, and grow that account during the initial onboarding period.
• Always Build Pipeline: Source around 20-30% of your own pipeline and multithread all the time.
• Challenge the Status Quo: Lead conversations with insights, tailor messages, and create urgency to drive deals forward.
• Demonstrate Curiosity and Compassion: Ask targeted questions, listen to understand concerns, and build consensus.
• Multi-Threaded Stakeholder Engagement: Build relationships across multiple stakeholders and drive organizational alignment.
• Pipeline Qualification Discipline: Apply MEDDPICC qualification rigor to every deal and maintain forecast accuracy.
• Partner Cross-Functionally: Collaborate with internal teams to optimize offerings based on client feedback.
• In-Person Prospect Engagement: Dedicate up to 50% of your time to travel for face-to-face meetings and cold prospecting.
• Operational Excellence & CRM Discipline: Maintain meticulous Salesforce discipline.
• Manage Your Territory: Build and execute a territory plan prioritizing accounts by opportunity size and strategic fit.
• Leverage AI Tools: Use AI-powered tools to research prospects and accelerate productivity.

Qualifications

• 8+ years of B2B sales experience, including 2+ years in enterprise sales, account management, or a related role.
• Strong background in developing and executing tactics to pitch solutions, negotiate, and close.
• Experience selling into K-12 school districts, government agencies, or public sector organizations is a plus.
• Track record of consistently exceeding targets and achieving measurable results.
• 5+ years prospecting by phone or in the field.
• Experience negotiating B2B contracts with multiple stakeholders.
• Proven experience communicating with Superintendents, Directors, and C-suite stakeholders.
• Proven Challenger sales experience and mentality.
• Comfortable traveling up to 50% and managing a high-volume field schedule.
• Proven experience leveraging AI-based or AI-enhanced sales tools.

Requirements

• Motivated by results and thrives in dynamic environments.
• Ability to establish new relationships and drive sales growth.
• Expertise in pitching, negotiation, and closing.

Benefits

• Equity for every full-time employee.
• Flexible vacation.
• Medical, dental, vision, and life insurance.
• 401(k) and FSA.
• Opportunity to work for a VC-backed company with significant upside potential.
• Remote position with compensation aligned to location.
• Total compensation includes equity stock options.

Company Description

HopSkipDrive is a leader in safe, fast, and simple supplemental student transportation, connecting kids to highly-vetted caregivers. Founded by three moms, we have facilitated over five million rides across 20 states and continue to grow rapidly.