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Strategic Account Executive

HopSkipDriveRemote USA Sales
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Salary
Not listed
Job type
Full-time
Work mode
Remote
Posted
18 Jun 2026
Status
Open · checked 7d ago

About this role

Role Overview

The Strategic Account Executive position at HopSkipDrive is a remote opportunity for a driven professional to secure net-new business and expand student transportation solutions across school districts and government agencies. This role suits an experienced sales expert who thrives in a fast-paced environment and embraces AI-driven workflows.

Key Responsibilities

Close new business by effectively negotiating contract terms, converting clients post-onboarding, and growing accounts.
Build a strong pipeline by self-sourcing 20% to 30% of pipeline opportunities and multi-threading across organizations.
Lead conversations with actionable insights rather than standard pitches, tailoring messages to distinct buyer personas and taking control of the sales process.
Engage stakeholders simultaneously across transportation, operations, finance, and executive leadership to align the buying committee.
Apply MEDDPICC qualification rigor to all deals, identify true economic buyers early, and maintain forecast accuracy in Salesforce.
Dedicate up to 50% of working time to field travel, including face-to-face meetings, follow-ups, and cold prospecting at district offices.
Utilize AI-powered tools such as Gong, Salesforce Agentforce, and Claude for prospect research, call preparation, and deal risk analysis.

Requirements

Bring 8+ years of B2B sales experience, including at least 2 years in enterprise sales or account management.
Demonstrate 5+ years of hunting and prospecting experience, utilizing cold calling, field drops, and related outreach techniques.
Execute professional field sales skills with the willingness and ability to travel up to 50%, including overnight trips.
Show proven experience in contract negotiation, RFP navigation, and communicating effectively with C-suite executives and superintendents.
Possess a challenger sales mentality to constructively reframe buyer assumptions and build urgency.
Exhibit fluency in leveraging AI-based or AI-enhanced sales tools to optimize the sales cycle.

Nice to Have

Prior experience selling into K-12 school districts, public sector organizations, or government agencies.

Skills and Tools

Enterprise B2B Sales
Pipeline Generation and Prospecting
Contract Negotiation and Closing
MEDDPICC Qualification
Salesforce CRM
AI Tools (Gong, Salesforce Agentforce, Claude)
Executive Communication and Field Sales

Salary and Benefits

Base salary of $95,000 with a total on-target earnings (OTE) of $160,000.
Company equity stock options for all full-time employees.
Comprehensive benefits package including medical, dental, vision, and life insurance.
Flexible vacation policy, 401(k) plan, and Flexible Spending Account (FSA).

About the Company

HopSkipDrive is a leading supplemental student transportation network founded by three moms to solve real-world mobility challenges. The company connects children with vetted caregivers on wheels and provides specialized software to school districts nationwide. Having facilitated over five million rides across more than 20 states, HopSkipDrive is backed by Series D funding and has raised $100M to date. The organization integrates AI directly into everyday operations and is recognized on the Inc. 5000 and Deloitte Fast-Growing Technology lists.

How to Apply

Interested candidates should visit the official HopSkipDrive careers page to submit an application for this remote position.

Questions candidates ask

Is this a remote position?

Yes, this role is remote within the USA, though it requires up to 50% travel for field prospecting and in-person meetings.

What is the salary and OTE for the Strategic Account Executive?

The base salary is $95,000 with a target OTE of $160,000, supplemented by equity stock options and full benefits.

What level of experience is required?

Candidates must have 8+ years of B2B sales experience, including at least 2 years in enterprise sales or account management, alongside 5+ years of prospecting experience.

What tools and technologies are used in this role?

Sales professionals use Salesforce for CRM discipline alongside AI tools like Gong, Salesforce Agentforce, and Claude for research and productivity.

What is the travel requirement for this job?

The role requires dedicating up to 50% of working time to travel, including overnight stays, for territory coverage and face-to-face prospect engagement.

Ready to apply?

The application is on the official HopSkipDrive careers page.

Apply on company site