Sales Representative (January Onboarding)

Sorry, this job was removed at 08:11 p.m. (CST) on Monday, Jan 26, 2026
Be an Early Applicant
Chicago, IL, USA
In-Office
45K-50K Annually
Logistics • Software • Transportation
The Role
ARE YOU INTERESTED IN JOINING AN INNOVATIVE LOGISTICS TECHNOLOGY COMPANY?

Loadsmart is a growth-stage technology company valued at over $1 billion (a true Tech Unicorn)!

We are a collection of industry veterans and user-centered engineers using innovative technology to fearlessly reinvent the future of freight by helping shippers, brokers, warehouses and carriers to move more with less.

With headquarters in Chicago and a globally distributed remote team, Loadsmart continues to attract top talent committed to driving meaningful change. We seek professionals who embody our core values: curiosity, clarity, results, commitment, and teamwork.

We are looking to add an Account Executive who thrives in a dynamic and fast-paced global company. This position will work closely with the operations team seeking new relationships through cold calling and nurturing established relationships.

DEPARTMENT: Account Sales
LOCATION: Chicago, IL (Onsite) 
Job Type: Exempt

WHAT YOU GET TO DO:

  • Actively prospect new business opportunities with high-volume outreach via cold calls, email, LinkedIn, and on-site or virtual meetings to build a pipeline of customers to sell FTL, Intermodal, and other logistics services
  • Actively manage existing clients to increase bookings, margins, and customer satisfaction
  • Identify key decision makers and business drivers, and relentlessly present the Loadsmart pitch in a compelling way
  • Adeptly guide customers through integration projects, contracts, RFPs, and onboarding processes.
  • Exhibit utmost dedication to constantly refining your sales skills. Practice frequent role play, objection handling exercises, and pitch demos. Actively seek and apply constructive feedback and data analysis observations to constantly refine your approach.
  • Become a subject matter expert on our business, including processes, operations, the competitive landscape, and remaining up-to-date on industry news. Insightfully evaluate Loadsmart’s current product offerings and roadmap. Actively share customer feedback and your own observations with Loadsmart Product and Engineering teams to enhance value for your customers.

REQUIRED QUALIFICATIONS:

  • Entry-level candidates are encouraged to apply. We're seeking individuals with 0-1+ years of sales experience or relevant coursework. 
  • You have proven relationship skills with solid negotiation capabilities and demonstrated influencing skills
  • Looking for motivated, high-energy individuals with excellent communication skills who will thrive high a pressure and fun environment
  • You are a driven, enthusiastic, and collaborative team player with a sense of urgency

WORKING AT LOADSMART:

• Competitive base salaries - we believe in rewarding top talent 
• Extremely competitive Equity package - become a shareholder in our company!
• Loadie Time Off - PTO and sick days without a limit
• Comprehensive Medical, Dental, and Vision insurance plans
• 401k Match 

At Loadsmart, we believe our biggest asset is our people. We are proud to be an equal opportunity employer, hiring and developing individuals from diverse backgrounds and experiences to add to our collaborative culture. Loadsmart treats all candidates and employees with respect and does not discriminate in our recruiting, hiring, and promoting processes, including on the basis of race, color, religion, sex, age, sexual orientation, gender identity and/or expression, national origin, veteran status, or disability.

It is the policy of Loadsmart that all offers of employment made shall be contingent upon successful completion of electronic background check(s). These checks will be job-related, consistent with business necessity and conducted by our vendor, pursuant to all applicable laws, rules, policies and procedures of our candidates' specific locale.

Loadsmart Compensation & Benefits Highlights

The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Loadsmart and has not been reviewed or approved by Loadsmart.

  • Leave & Time Off Breadth Unlimited PTO (“Loadie Time Off”) and sick time are described in postings as available without a limit, broadening flexibility for time away. Availability is noted across many U.S. roles, though exact application can vary by position and location.
  • Healthcare Strength Comprehensive medical, dental, and vision coverage is consistently cited in job postings, indicating a solid core health offering. This breadth forms a standard tech-style benefits baseline for U.S. employees.
  • Equity Value & Accessibility Stock options are frequently offered and positioned as competitive alongside base pay and other benefits. This ownership component is presented as a meaningful part of total rewards.

Loadsmart Insights

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The Company
HQ: Chicago, IL
732 Employees

What We Do

We are industry veterans and data-scientists using innovative technology to fearlessly reinvent the future of freight. As the ‘nerds of logistics’, we seek intelligence in data to solve deep-rooted inefficiencies in the industry. We give shippers, brokers and carriers access to our data connections (linking supply and demand) and suite of award-winning solutions to strike the perfect balance of cost and service. We’re creating a more efficient and environmentally responsible way to move more with less. For more information, please visit: https://loadsmart.com

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