Strategic Account Executive

PrePass

4h

About The Position

We are seeking an Enterprise / Strategic Account Executive to drive net-new revenue growth across large, complex fleet organizations operating 1,000+ vehicles. In this role, you will own the full sales cycle for enterprise and national accounts, partnering with executive leadership and cross-functional stakeholders to deliver measurable operational and financial outcomes. You will serve as a strategic advisor, aligning PrePass’s weigh station bypass, toll management, and safety solutions to enterprise-level efficiency, compliance, and cost-reduction initiatives. This role is highly visible, cross-functional, and critical to accelerating PrePass’s expansion within the largest fleets in North America.

Requirements

• 5+ years of B2B sales experience, including experience managing complex or large accounts
• Proven success closing multi-stakeholder, multi-year commercial agreements
• Experience selling into transportation, logistics, fleet technology, SaaS, or adjacent industries preferred
• Demonstrated ability to engage operational and executive-level stakeholders
• Strong business acumen with the ability to articulate financial and operational value
• Experience navigating contract negotiations and procurement processes
• Consistent track record of meeting or exceeding sales targets
• Excellent communication, presentation, and negotiation skills

Nice To Haves

• Experience selling technology solutions to fleets operating 1,000+ vehicles
• Familiarity with weigh station bypass, toll management, safety technology, or compliance solutions
• Background in SaaS or subscription-based revenue models
• Experience using Salesforce or similar CRM platforms to manage complex enterprise pipelines

Responsibilities

• Drive net-new enterprise revenue by identifying, engaging, and closing large fleet organizations (1,000+ vehicles)
• Develop and execute strategic account plans to penetrate complex, multi-entity fleet structures
• Generate and advance high-value opportunities through targeted outbound prospecting and executive engagement
• Partner with marketing and sales leadership to execute account-based strategies within named enterprise accounts
• Own the full enterprise sales cycle, including discovery, solution alignment, executive presentations, business case development, pricing strategy, and contract execution
• Lead multi-threaded engagement across operations, safety, finance, procurement, and executive leadership teams
• Structure and negotiate multi-year commercial agreements that deliver strong customer value and favorable business outcomes
• Maintain accurate forecasting, pipeline hygiene, and executive-level visibility within PrePass sales systems
• Serve as a strategic advisor on bypass, tolling, safety, and compliance trends impacting large fleets
• Quantify ROI and develop executive-ready business cases that align PrePass solutions to enterprise operational KPIs
• Navigate complex procurement processes and align with enterprise technology, compliance, and financial frameworks
• Build long-term executive relationships that position PrePass as a trusted, enterprise-scale partner
• Partner with solutions consulting, product, marketing, analytics, and revenue operations to accelerate deal velocity and strengthen value positioning
• Provide enterprise market insights to inform product strategy and go-to-market improvements
• Support seamless transition from sale to customer success to ensure strong adoption and expansion opportunities

Benefits

• Robust benefit package that includes medical, dental, and vision that start on date of hire.
• Paid Time Off, to include vacation, sick, holidays, and floating holidays.
• Paid parental leave.
• 401(k) plan with employer match.
• Company-funded “lifestyle account” upon date of hire for you to apply toward your physical and mental well-being (i.e., ski passes, retreats, gym memberships).
• Tuition Reimbursement Program.
• Voluntary benefits, to include, but not limited to Legal and Pet Discounts.
• Employee Assistance Program (available at no cost to you).
• Company-sponsored and funded “Culture Team” that focuses on the Physical, Mental, and Professional well-being of employees.
• Community Give-Back initiatives.
• Culture that focuses on employee development initiatives.
• Company-wide bonus and commission plans.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed