Sr. Regional Account Manager

About the role

This Senior Regional Account Manager role centers on owning the day-to-day management and long-term strategic direction of a Tier 1 book of business for HopSkipDrive. The hire will be accountable for retention, expansion, and overall account health while acting as the strategic quarterback for complex school districts. They will spearhead enterprise growth by driving strategic expansion across the product suite through structured discovery and Challenger methodology. This position requires advanced client communication, strong commercial acumen, and operational rigor to influence both internal and external stakeholders. The successful candidate will partner cross-functionally with Sales, Operations, Product, Finance, Trust & Safety and Support to align on client priorities and optimize offerings.

Key facts

What you'll do

• In-Person Client

Engagement: Dedicate 2 to 3 days each week to on-site client visits to foster relationships, deepen understanding of client needs, and drive meaningful engagement, with additional national travel as needed and reliable transportation required.

• Spearhead Enterprise Growth: Drive strategic expansion across HopSkipDrive's product suite through structured discovery and Challenger methodology, building and executing district-level growth strategies that include multi-threaded stakeholder plans while owning retention, expansion, and overall performance of named accounts.
• Manage Client Accounts: Deliver exceptional client service and build and maintain strong, multi-threaded relationships across operational, technical, and executive stakeholders to ensure account health and satisfaction.
• Seek Net-New Opportunities: Lead multi-department discovery within districts to uncover unmet needs and quantify opportunity, leveraging structured discovery and Challenger methodology to drive expansion across the product suite.
• Communicate Tailored Value: Communicate confidently with client executives, influencing decision-making through data, insight, and outcome-based recommendations that address specific district challenges.
• Partner Cross-Functionally: Align Sales, Operations, Product, Finance, Trust & Safety and Support around client priorities to optimize offerings and execution in collaboration with internal teams.
• Lead Pricing Discussions: Lead renewals and expansions, including structured negotiations and closing motions to secure favorable outcomes for both the client and HopSkipDrive.
• AI Enabled Operational Excellence: Utilize AI to craft personalized meeting agendas, synthesize complex stakeholder inputs, and drive operational efficiency across the account management lifecycle.
• Orchestrate Strategic Planning: Develop and own comprehensive account plans that outline objectives, key initiatives, and success metrics to guide long-term client relationships.
• Drive Outcome-Focused Reviews: Establish and monitor key performance indicators to demonstrate value and impact, using insights to refine strategies and renewals.
• Coordinate Cross-Team Execution: Serve as the central point of contact for internal teams to resolve issues, streamline processes, and ensure timely delivery of services.
• Maintain Stakeholder Mapping: Continuously update influence and decision-maker maps to ensure aligned engagement strategies and targeted outreach.
• Lead Executive Sponsorship: Cultivate and maintain executive-level relationships to reinforce trust and strategic alignment with district leadership.
• Ensure Compliance and Safety: Partner with Trust & Safety to uphold all operational standards and compliance requirements within client engagements.

Requirements

• You must have reliable transportation to accommodate 2 to 3 days of weekly in-person client visits and occasional national travel.
• You must be legally authorized to work in the United States without sponsorship now or at any time during the duration of this role.
• You must have a proven track record of managing and growing complex, enterprise-level accounts in a SaaS or technology environment.
• You must have experience using data and insight to drive strategic account planning and stakeholder influence.
• You must have experience with Challenger sales methodology and consultative selling in a B2B context.
• You must have strong commercial acumen, including demonstrated ability to lead pricing discussions and negotiations.
• You must have advanced written and verbal communication skills for executive-level audiences.
• You must have experience leveraging technology, including AI tools, to enhance operational efficiency and client engagement.
• You must be able to synthesize complex information and translate it into clear, actionable recommendations for stakeholders.
• You must thrive in a fast-paced, mission-driven environment where adaptability and ownership are essential.
• You must be comfortable managing multiple priorities and stakeholders in a distributed, remote work setting.
• You must be willing to adopt and champion new ways of working that integrate AI into daily workflows.
• You must have a history of collaborating with cross-functional teams to solve customer problems and drive outcomes.
• You must have a strong commitment to safety, compliance, and ethical standards in all client interactions.