Job Description

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.

Essential Job Functions

• 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 customer 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.

Travel Requirements

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

The above description covers the most significant duties performed but does not include other related occasional work that may be assigned or is completed by the employee.

Position Requirements

• 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 questions to uncover business needs and sales opportunities.

• Familiarity with CRM systems like Salesforce.com is a plus.

• Customer Focus

• Learning Agility

• Collaboration and Teamwork

• Communication and Influence

• Resilience and Adaptability

Essential Job Functions

• Contact assigned prospective businesses daily via phone, email, trade shows

• Consult with prospects to determine your financial needs, provide expert guidance and pitch Truckstop.com Factoring services accordingly

• Maintain lead / prospect sales records in the CRM database

• Identify new sources of prospects - prepare action plans and schedules to reach specific geographical regions, industries of prospective clients

• Development a group of reliable referral sources

• Assess prospective clients' Accounts Receivable & Aging information to determine relevant factoring options for their business

• Work with multiple internal departments to create relevant financial services proposals and contracts for prospective clients

• Work as a team in follow up on your customers' services and provide new service opportunities as needed

• Work as a sales leader to refine sales tactics to meet / exceed monthly / quarterly / annual benchmark quota goals

• Protect company and customer information in accordance with company policies and procedures

The above description covers the most significant duties performed but does not include other related occasional work that may be assigned or is completed by the employee.

Position Requirements

• High school diploma or equivalent

• Proficient in Microsoft Office (Outlook, Excel, Word) and use of office equipment

• Strong written and verbal communication skills

• The ability to comprehend, retain and apply complex regulatory & factoring information

• Able to perform repetitive tasks

• Good organization and record keeping skills required

• Email, MS Office (Word & Excel) CRM database skills required

• Customer service experience preferred

• Sales experience preferred - including persuasiveness, communication, energy, undeterred by rejection

• Experience with transportation, factoring, financing, or banking preferred

The above description covers the most significant duties performed but does not include other related occasional work that may be assigned or is completed by the employee. 

Truckstop provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state, or local laws. 

Truckstop participates in the E-Verify program. Learn more about the E-Verify program here: https://www.e-verify.gov/

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