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Senior Business Development/Sales Representatives - Fleet Safety Technology

L5

my fleet aiChicago, ILyesterday

Occupations

Sales Representatives of Services, Except Advertising, Insurance, Financial Services, and TravelSales Representatives, Wholesale and Manufacturing, Except Technical and Scientific ProductsSales Representatives, Wholesale and Manufacturing, Technical and Scientific Products

Industries

All Other Insurance Related ActivitiesGeneral Freight Trucking, Long-Distance, Less Than TruckloadGeneral Freight Trucking, Long-Distance, Truckload
MyFleetAI | Remote – Generous Commission Structure About MyFleetAIMyFleetAI is a technology company providing comprehensive fleet safety, training, and compliance solutions to the trucking and transportation industry. Its S.A.F.E. platform combines driver training, AI-enabled safety monitoring, camera-event validation, ELD compliance, driver coaching, safety scoring, and incident management into an integrated safety program. The company also provides specialized solutions for insurance carriers, helping them monitor fleet risk, improve loss control, and strengthen safety performance across their insured fleets. Learn .
The Opportunity:
  • MyFleetAI is seeking highly experienced, well-connected sales professionals to expand its business across the U.S. transportation, commercial insurance, and government markets.
  • This is a fully remote opportunity, open to qualified candidates throughout the United States.
  • We are looking for proven sales professionals who know these industries, understand how purchasing decisions are made, and have established relationships with key decision-makers.
  • Our target markets include:
  • Private Trucking Fleets and Motor Carriers: Small, midsize, and large commercial fleets.
  • Insurance Companies: Commercial auto insurers, transportation insurance providers, MGAs, and organizations insuring trucking and logistics operations.
  • State Departments of Transportation: Fleet safety, driver training, compliance, and related programs.
  • Federal Government: Including the Department of War, FMCSA, and other agencies responsible for vehicle fleets, transportation safety, and compliance.
Required Qualifications: Minimum 10 years of successful sales experience selling into one or more of the target markets listed above. Established industry contacts and relationships with relevant decision-makers. Deep understanding of the trucking, transportation, fleet safety, commercial insurance, or government sectors. Demonstrated success developing new business, managing relationships, negotiating contracts, and closing sales. Ability to work independently, generate opportunities, and aggressively pursue new accounts in a remote environment. Direct experience selling into at least one of these markets is mandatory. We are not seeking generalist salespeople who would need to learn the industry or build their contacts from scratch.
Compensation: This is a 100% commission-based position offering a 25% commission of sales designed to reward experienced sales professionals who can originate and close business. We are particularly interested in established professionals with the industry knowledge, relationships, and initiative to generate substantial new business.
Interested Candidates: Please submit your resume along with a brief description of your relevant industry sales experience, established relationships, and the markets you have successfully sold into.
Apply now (opens in a new tab)
Apply now (opens in a new tab)

Level

SeniorL5

Location

Chicago, IL

Occupation

Sales Representatives of Services, Except Advertising, Insurance, Financial Services, and Travel

Industry

All Other Insurance Related Activities

Posted

yesterday

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