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Strategic Account Executive at PrePass. About PrePass. . PrePass® is North America's most trusted weigh station bypass and toll management platform. We’re transforming how the transportation industry operates—creating solutions that keep trucks moving safely, efficiently, and compliantly. This means making bold decisions and building scalable systems that support not only fleets but the broader economy. It all starts with enabling commercial vehicles to keep rolling through seamless toll management, weigh station bypass, and safety solutions. It’s what we do best, and we do it to meet the demands of the road every day..  . That’s why people join us: our solutions operate in real time on highways and interstates across the nation, helping fleets go farther, faster. This work is high-impact and complex, requiring thoughtful leadership, strong execution, and a deep understanding of customer and business needs. We hire bold thinkers with a heart for impact, a passion for progress, and the optimism to shape the future of transportation.. About the Role. 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.. Essential Responsibilities. Enterprise Revenue Growth & Strategic Prospecting. 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. Complex Deal Leadership & Sales Execution. 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. Consultative Enterprise Engagement. 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. Cross-Functional Collaboration & Market Feedback. 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. What Success Looks Like. Establish trusted advisor relationships with C-level and senior operational leaders within large fleet organizations. Consistently generate and advance high-quality enterprise pipeline aligned to revenue targets. Successfully close complex, multi-stakeholder, multi-year agreements. Demonstrate deep expertise in fleet operations, compliance dynamics, toll programs, and enterprise technology adoption. Contribute to the development of scalable enterprise sales strategies and best practices. 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. Bonus Points For. · 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. Desired Characteristics. · Strategic thinker with strong account planning and long-cycle deal management skills. · Executive presence with the ability to influence senior decision-makers. · Highly disciplined in pipeline development and forecasting accuracy. · Comfortable navigating ambiguity and complex organizational structures. · Self-motivated, competitive, and driven to build enterprise-level impact. · Collaborative mindset with a commitment to contributing to a high-performance sales culture. Company Location: United States.