Sr. Regional Account Manager
$90,000–$100,000 year
On-site · Remote, Oregon, United States
Job Summary
Sr. Regional Account Manager responsible for day-to-day account management and long-term strategy across a Tier 1 book of business for HopSkipDrive. Key duties include 2-3 days per week of on-site client engagements with potential additional travel, spearheading enterprise growth through district-level strategic plans, managing client accounts and multi-stakeholder relationships across operational, technical, and executive stakeholders, uncovering net-new opportunities through multi-department discovery, communicating tailored value to client executives, cross-functional partnership with Sales/Operations/Product/Finance/Trust & Safety/Support, leading renewals and expansions negotiations, and leveraging AI to craft meeting agendas, summarize Salesforce data, and automate recurring reporting. The role emphasizes Challenger-led selling, data-driven insights, and high operational rigor in a remote-first environment with regional on-site requirements. Compensation includes a base of $90,000-$100,000 with an OTE of $150,000-$170,000, equity, and full-time benefits; role is remote and includes 2-3 days on-site visits regionally. Travel and on-site presence are required as part of the responsibilities.
Required Qualifications
- 8+ years of experience in Account Management, Customer Success, or Consultative Sales in SaaS, marketplace, logistics, or services environments.
- Proven ownership of retention and expansion revenue.
- Strong executive communication and presentation skills.
- Demonstrated success managing complex, multi-stakeholder accounts.
- Advanced CRM discipline and data fluency (Salesforce or equivalent).
- Experience leading cross-functional account execution.
- Comfort operating in ambiguity with accountability for outcomes.
- Experience in education, government, or regulated markets highly preferred
- Familiarity with Challenger or similar insight-led sales methodologies highly preferred
- Background in transportation, logistics, or marketplace platforms highly preferred
- High operational rigor and the ability to leverage AI into daily workflows
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