Account Executive

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 systems that support not only fleets but the broader economy. It all starts with enabling commercial vehicles to keep rolling with 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 are implemented in real-time, on highways and interstates across the nation, helping fleets go farther, faster. This work challenges and rewards, presenting complex problems that need ambitious answers. 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

PrePass is looking for a consultative closer to drive new business, grow revenue, and help build a new Account Executive motion in the SMB segment. In this role, you’ll own the full sales cycle, from prospecting to close, for larger and more complex opportunities among fleets with 1–49 trucks. These are the deals that don’t close on the first call and need a strategic, persistent owner to get them across the finish line. You’ll focus on identifying right-fit customers and clearly demonstrating the value of our solutions. The ideal candidate has experience selling to SMBs, is comfortable in a high-velocity sales environment, and thrives in a fast-paced, competitive landscape.

You’ll work qualified opportunities routed from our Lead Development Representatives and Sales Specialists, run disciplined multi-touch cadences, and partner closely with our Upmarket Account Executives on deals that cross segment lines, coordinating handoffs, sharing account insights, and aligning on strategy so every customer has the right owner as fleets grow or shift between segments. You’ll also bring a strategic lens to how we scale the SMB AE motion, sharing frontline insights that sharpen our approach, strengthen best practices, and drive consistent results as the team grows.

Key Responsibilities

Pipeline & Close

- Own the full sales cycle for qualified SMB opportunities—discovery, solution design, proposal, negotiation, and close—with a focus on larger fleets and deals that extend beyond the initial speed-to-lead window.
- structured, multi-channel cadences (phone, email and virtual meetings) to re-engage prospects who are interested but not yet ready to buy.
- Lead consultative conversations that uncover a fleet’s route, toll, safety, and compliance needs, then build a clear business case for PrePass solutions.
- Deliver tailored virtual presentations and proposals that connect PrePass value to time, fuel, and cost savings for the customer.
- Meet or exceed monthly targets for net new revenue, booked trucks, and opportunity conversion.

Revenue Recovery & Account Growth

- Convert reactivation and upgrade opportunities into incremental revenue, including win-backs of former PrePass customers.
- Build strategic re-engagement plans for aged, nurture, and closed-lost opportunities with legitimate revenue potential.
- Identify expansion opportunities within assigned accounts, such as additional trucks, additional DOT numbers, and service upgrades.
- Partner with larger-fleet sales teams to co-sell or transition opportunities approaching 50+ trucks, ensuring full context and a seamless customer experience.

Forecasting & Sales Discipline

- Manage a healthy, accurate pipeline in our dedicated CRM with current stages, close dates, and next steps on every opportunity.
- Deliver reliable weekly forecasts and participate in regular pipeline reviews with the Sales Manager.
- Follow established rules of engagement, SOPs, and handoff standards across LDR, Sales Specialist, and AE roles.
- Leverage dedicated systems to maximize productivity, conversion, and pipeline velocity.

Cross-Functional Collaboration

- Receive handoffs from LDRs and Sales Specialists, ensuring timely first contact and a seamless transition for the prospect.
- Partner with Enrollment Support, Customer Success, and Onboarding to resolve credential and documentation gaps and deliver clean post-sale transitions that set new customers up for long-term success.
- Share market, competitor, and objection insights with Sales leadership, Marketing, and Sales Enablement to strengthen messaging and process.

Requirements

Qualifications

- 5+ years of B2B sales experience, account management, or a similar role.
- Proven track record of meeting and exceeding quota.
- Experience managing a multi-stage pipeline with deals that close over weeks, not only on a single call.
- Strong discovery, presentation, negotiation, and objection-handling skills.
- Proficiency with CRM systems (Dynamics 365 preferred) and sales engagement or dialer tools.
- Proficiency in Microsoft Office, including Word, Excel, PowerPoint, Teams, and Outlook.
- Excellent verbal and written communication skills with a confident phone and virtual presence.

Bonus Points For:

- Sales experience in transportation, logistics, fleet technology, telematics, or SaaS.
- Experience selling to owner-operators and small business owners.
- Familiarity with trucking credentials and regulations (e.g., USDOT, FMCSA, IFTA, UCR) or toll management.
- Hands-on-experience with Outreach, Five9, or LeanData
- Bilingual in English and Spanish.

Desired Characteristics

- Persistent and resilient; views follow-up as a competitive advantage.
- Highly organized, with strong pipeline and time management discipline.
- Consultative and curious; asks great questions and listens to understand.
- Builder mindset; comfortable navigating ambiguity in a first-of-its-kind role.
- Coachable and data-driven, with a high degree of ownership and accountability.
- Team-first collaborator who builds trust across functions.

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.
- 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.

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.