Sales Representative

Loadsmart; Chicago (IL); On-site; USD 45,000 - 50,000; Full time

Benefits offered by this job

Competitive base salary

Equity package

Medical, Dental, Vision insurance

401k match

PTO and sick days with managerApproval

Disability Insurance 100% covered

Teledoc & Talkspace coverage

Commuter benefits

Onboarding & career progression

Job summary

Loadsmart, a hyper-growth logistics tech company in Chicago, seeks an Account Sales professional to build a high-volume pipeline for FTL and intermodal services.

This onsite role prioritizes relationship-building, closing deals, and navigating complex onboarding processes with clients.

Qualifications

• Entry-level candidates are encouraged to apply (0–1+ years of sales experience or relevant coursework).
• Proven relationship skills with negotiation abilities.
• Excellent communication skills in a high-energy, results-driven environment.
• Driven, enthusiastic, collaborative team player with urgency.

Responsibilities

• Prospect new business via cold calls, email, LinkedIn, and on-site or virtual meetings to build a pipeline of customers for Loadsmart services.
• Manage existing clients to increase bookings, margins, and customer satisfaction.
• Identify key decision makers and compellingly present Loadsmart's pitch.
• Guide customers through integration projects, contracts, RFPs, and onboarding processes.
• Refine sales skills through role play, objections, and data-driven feedback.
• Stay informed on Loadsmart products, roadmap, and industry trends; share feedback with Product and Engineering.

Skills

Relationship skills

Negotiation

Communication skills

Team player

Job description

ARE YOU INTERESTED IN JOINING A HYPER-GROWTH LOGISTICS TECH COMPANY?

Loadsmart is a growth‑stage start‑up technology company valued at over $1 billion (a tech unicorn), led by a leadership team of logistics veterans and experienced engineers, product leaders and data scientists continuing to disrupt this $800 billion industry.

Department: Account Sales

Location: Chicago, IL (Onsite)

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!
• Comprehensive Medical, Dental, and Vision insurance plans
• 401k Match up
• Loadie Time Off – PTO and sick days without a limit with Manager approval
• Short and Long Term Disability Insurance covered 100% by the company
• Teledoc (remote doctors) and Talkspace (mental health counseling) membership fees covered 100% by the company
• Commuter benefits and membership with CITI (NYC)/Divvy bike (CHI).
• All of our team goes through a 10‑week onboarding training, assigns an internal buddy to help you navigate your way around, and continuous education to help you further your career
• We offer career paths with quarterly developmental reviews, promotions, and raises (based on your performance; ask your recruiter about our automatic CLEAR career progression program!)

Apply Today!

Job Type: (Exempt)

45,000 - 50,000 a year

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.

We may use artificial intelligence tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.