Strategic Account Executive
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Job Description
Enterprise Account Executive responsible for driving revenue growth in large fleet organizations. Partnering with executive leadership and delivering measurable outcomes through strategic sales execution.
Responsibilities:
- **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:
- 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
Benefits:
- **How We Will Take Care of You**
- 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.
- Join Us**At PrePass, our mission drives us.**
- We invest in relationships. We challenge ourselves to innovate and improve. We win together. Simply put, we live our Core Values.
- **Ready to help move the transportation industry forward? Join us and let’s drive progress—together.**
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