Senior Regional Account Manager

This is a fully remote position, open to applicants in United States.

📋 Description

• Allocate 2-3 days per week for on-site visits to clients to strengthen relationships, enhance understanding of their needs, and promote meaningful engagement.

• Propel strategic growth across HopSkipDrive’s product range using structured discovery and the Challenger methodology.

• Develop and implement district-level growth strategies, including comprehensive stakeholder plans while managing retention, expansion, and overall performance of designated accounts.

• Provide outstanding client service and cultivate robust, multi-threaded relationships with operational, technical, and executive stakeholders.

• Facilitate multi-departmental discovery within districts to identify unmet needs and quantify potential opportunities.

• Communicate assertively with client executives, influencing their decision-making through data-driven insights and outcome-focused recommendations.

• Synchronize efforts across Sales, Operations, Product, Finance, Trust & Safety, and Support in alignment with client priorities, optimizing our offerings accordingly.

• Oversee renewals and expansions, including structured negotiations and closing processes.

• Leverage AI to create tailored meeting agendas, synthesize complex stakeholder requirements, and draft impactful follow-up communications.

⛳️ Requirements

• 8+ years of experience in Account Management, Customer Success, or Consultative Sales within SaaS, marketplace, logistics, or service environments.

• Demonstrated ownership of retention and expansion revenue.

• Exceptional executive communication and presentation abilities.

• Proven success in managing complex, multi-stakeholder accounts.

• Advanced CRM proficiency and data fluency (Salesforce or similar).

• Experience in leading cross-functional account execution.

• Ability to navigate ambiguity while being accountable for results.

• Experience in education, government, or regulated markets is highly preferred.

• Familiarity with Challenger or other insight-driven sales methodologies is highly preferred.

• Background in transportation, logistics, or marketplace platforms is highly preferred.

• Strong operational rigor and capability to integrate AI into daily workflows.

🏝️ Benefits

• Equity

• Flexible vacation

• Medical, dental, vision, and life insurance

• 401(k)

• FSA