Sr. Regional Account Manager (SaaS)

TL;DR

Sr. Regional Account Manager (SaaS/Logistics): Managing a Tier 1 book of business to drive retention and expansion through strategic account planning and Challenger-led selling with an accent on building multi-threaded relationships with school districts. Focus on delivering measurable outcomes, leading complex renewal negotiations, and leveraging AI for operational excellence.

Location: Remote (USA), but requires 2-3 days of on-site client visits regionally

Salary: $90,000–$100,000 base, OTE $150,000–$170,000 + equity

Company

A Series D VC-backed company and leader in supplemental student transportation, utilizing an AI-forward marketplace to connect kids with vetted caregivers.

What you will do

• Own retention, expansion, and overall account health for a Tier 1 book of business.
• Conduct on-site client visits 2-3 days per week to deepen relationships and engagement.
• Build and execute district-level growth strategies using the Challenger methodology.
• Lead renewals and expansion negotiations, including structured closing motions.
• Partner cross-functionally with Sales, Product, Finance, and Operations to optimize client offerings.
• Utilize AI tools to automate reporting, summarize Salesforce data, and synthesize stakeholder needs.

Requirements

• 8+ years of experience in Account Management, Customer Success, or Consultative Sales within SaaS or logistics.
• Must be based in the USA.
• Proven success in owning retention and expansion revenue for complex, multi-stakeholder accounts.
• Advanced discipline in CRM data management (Salesforce or equivalent).
• Strong executive communication and presentation skills.
• High operational rigor and ability to integrate AI into daily workflows.

Nice to have

• Experience in education, government, or other regulated markets.
• Familiarity with Challenger or similar insight-led sales methodologies.
• Background in transportation, logistics, or marketplace platforms.

Culture & Benefits

• Equity stock options for all full-time employees.
• Comprehensive health benefits including medical, dental, vision, and life insurance.
• 401(k) and FSA.
• Flexible vacation policy.
• Remote-first, mission-driven environment with a high bar for execution.
• AI-forward culture with active investment in training and tool adoption.