Sr Account Executive, Broker Factoring

At Truckstop, we have transformed the entire freight-moving lifecycle with our SaaS solutions. From freight matching to payments and everything in between, we are the trusted partner for carriers, brokers, and shippers alike. We lead this industry forward with our One Team mindset committing to principles such as assume positive intent, have each other’s back, and be your authentic self. Our drive for greatness produces high expectations, yet our regard for humans is even higher.

Join a team of brilliant minds and generous hearts who care deeply about other's success.

The Sr Account Executive is a senior, individual contributor responsible for driving revenue across high-value broker and carrier accounts. This role owns complex, consultative sales cycles end-to-end while also acting as a trusted deal and customer resource for the broader sales organization. In partnership with the Director of Factoring, the Lead AE provides guidance on complex customer scenarios, supports strategic deal execution, and assists in the onboarding and ramp of new Account Executives.

Success in this role requires strong judgment, relationship building, and the ability to influence outcomes across both customers and peers.

• Own and deliver against monthly revenue targets by executing a full-cycle, outside sales motion across high-value broker and carrier accounts.
• Lead complex, consultative sales cycles involving multiple stakeholders, custom pricing considerations, and operational dependencies.
• Deliver compelling virtual and onsite product demonstrations that align platform capabilities to customers’ business outcomes.
• Travel regularly to customer locations, trade shows, and industry events to build pipeline, advance active deals, and strengthen market presence.
• Serve as a trusted deal, customer, and execution resource by partnering with the Director of Factoring to support complex deals, escalations, and strategic onboarding scenarios.
• Support the onboarding and early ramp of new Account Executives through hands‑on deal guidance, live customer participation, and real‑time coaching on product positioning and sales execution.
• Maintain disciplined pipeline management, forecasting accuracy, and activity tracking within Salesforce to support predictable revenue performance.
• Provide interim leadership support when necessary by conducting 1:1 check‑ins and assisting with deal execution during times when the Director of Factoring is unavailable, ensuring ongoing continuity for active deals and customer interactions.
• Contact assigned prospective businesses daily via phone, email, and trade shows.
• Consult with prospects to determine their financial needs, provide expert guidance and pitch  Factoring services accordingly.
• Maintain lead and prospect sales records in the CRM database.
• Identify new sources of prospects and prepare action plans and schedules to reach specific geographical regions and industries.
• Develop a group of reliable referral sources.
• Assess prospective clients’ accounts receivable and aging information to determine relevant factoring options for their business.
• Work with multiple internal departments to create relevant financial service proposals and contracts for prospective clients.
• Follow up on customer services and provide new service opportunities as needed.
• Refine sales tactics as a sales leader to meet or exceed monthly, quarterly, and annual benchmark quota goals.
• Protect company and customer information in accordance with company policies and procedures.

This role requires regular domestic travel, including industry trade shows, customer site visits across assigned territories, and in‑person onboarding for high‑value customers. Some overnight travel is expected. Travel is a recurring and essential component of the role, not occasional.

• Bachelor’s degree in business administration, sales, or a related field (preferred but not required).
• 5+ years of experience in factoring or logistics.
• Proven ability to understand and communicate the business value and functionality of software solutions.
• Skilled in handling objections and using probing…