Mid- Market Account Executive

Fleetworthy offers the only complete technology suite for fleet readiness, uniting safety and compliance, toll management, and weigh station bypass solutions. We help fleets streamline operations, control costs, and operate with confidence. Trusted by 75% of the top fleets in North America, Fleetworthy offers the most adopted toll management solution and largest weigh station bypass network. Going beyond regulatory requirements, our safety and compliance capabilities strengthen safety programs and enable proactive audit readiness.

We support millions of vehicles and drivers and are recognized across the industry for innovation and leadership. Fleetworthy is shaping the future of fleet readiness with AI-enabled, connected fleet technology that keeps drivers safe, fleets compliant, and operations running at peak efficiency. Learn more at

We are looking for a dynamic Strategic Mid Market Client Account Executive to join our Enterprise Sales Team and lead our sales strategy and execution among key prospects. This individual will be tasked with creating and implementing a strategic plan to grow the business and acquire new Fleetworthy customers across various verticals in the Enterprise account territory.

• Create and execute a plan for building a pipeline and selling into fleets of 100 to 750 vehicles.
• Understand the value of Fleetworthy services and how to properly position them with both over-the-road and service fleets.
• Assist customers in building a business case justification for the purchase of Fleetworthy services.
• Maintain an accurate record of activity and results in our  database.
• Accurately forecast your sales pipeline on a monthly and quarterly basis.
• Strive to meet and exceed established goals, timelines, and quotas.
• Work with Direct and Channel Sales, Account Management, Customer Success, Operations & Support teams to ensure complete customer satisfaction.
• Ensure relationships with key decision‑makers for accounts and prospects are continuously developed and nurtured.
• Travel when necessary (up to 20%).

• Minimum 3 years of solution selling experience.
• Ability to offer unique perspective by reframing and challenging the way customers view their business; know how to structure a sales pitch to highlight customer benefits before supplier strengths.
• Adept at driving two‑way communication by clearly articulating value proposition to customer’s pain points.
• Preferred experience in selling SaaS software solutions.
• Experience selling cross organizationally (C and VP levels).
• Proven proficiency at building and developing opportunity and territory plans.
• Experience in and ability to clearly articulate sales stages and process for complex accounts.
• Ability to identify business targets, secure appointments, and execute a strategic sales process.
• Excellent written and verbal communication skills, strong presentation skills.

Fleetworthy is committed to fostering a diverse and inclusive culture that is respectful and welcoming of individual differences. We are proud to be an equal opportunity employer and all qualified applicants will receive consideration for employment without regard to race, color, religion or belief (or lack thereof), sex, nationality, national or ethnic origin, civil status, age, citizenship status, sexual orientation, disability, genetic information, familial status, marital or registered civil partnership status, pregnancy or maternity status, gender identity, gender reassignment, military or veteran status, or any other protected characteristic in accordance with applicable laws and regulations.