Truckstop

SaaS

SrAccountExecutive

Wauwatosa, Wisconsin, United States; United States Remote Friendly
Market Sentiment
HIGH DEMAND

Neural analysis suggests this role is
optimal for Senior candidates.

The Brief

“Sr Account Executive at Truckstop. Skills: revenue generation, complex sales cycles, account management. 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”

What You'll Achieve.

Own and deliver against monthly revenue targets; Meet / exceed monthly / quarterly / annual benchmark quota goals; Maintain disciplined pipeline management, forecasting accuracy, and activity tracking within Salesforce to support predictable revenue performance

Industry & Context.

SaaS
Problems you'll solve

Learning Agility

Eligibility Requirements

Regular domestic travel required, 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

What They're Looking For.

Must Have

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, High school diploma or equivalent, Proficient in Microsoft Office (Outlook, Excel, Word) and use of office equipment, 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

Nice to Have

Bachelor’s degree in business administration, Sales, or a related field, Familiarity with CRM systems like Salesforce. com is a plus, Customer service experience preferred, Sales experience preferred - including persuasiveness, communication, energy, undeterred by rejection, Experience with transportation, factoring, financing, or banking preferred

What You'll Do.

Own and deliver against monthly revenue targets by executing a full-cycle

outside sales motion across high-value broker and carrier accounts

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

Serve as a trusted deal

and execution resource by partnering with the Director of Factoring to support complex deals

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

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

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

How You'll Work.

Team & Collaboration

Act as a trusted deal and customer resource for the broader sales organization; Partner with the Director of Factoring to support complex deals, escalations, and strategic onboarding scenarios; Support the onboarding and early ramp of new Account Executives; Work with multiple internal departments to create relevant financial services proposals and contracts; Work as a team in follow up on your customers' services and provide new service opportunities as needed

Communication Scope

written and verbal communication skills; Communication and Influence

Full 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.   Job Summary 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 li",201340122,"2",134233614,"true",469778129,"ulli",335572020,"1",469778324,"Normal"]}">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 t

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