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Posted May 12, 2026

Outside Sales Representative – 1099 Contractor

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Job Description: • *What success will look like:**As a 1099 Outside Sales Representative, you will operate as an independent contractor responsible for driving new business within your territory. This commission-based role is perfect for motivated, entrepreneurial individuals who thrive in a high-energy, target-driven environment.As an independent contractor with Whip Around, you’ll have the freedom to shape your own schedule and income potential while representing a leading-edge solution in the fleet management space. Contractors are responsible for their own expenses, including transportation, communication, and work-related equipment.You’ll focus on building relationships, showcasing Whip Around’s value, and closing deals with small to mid-sized businesses.- Identify and Target Prospects: Build a robust pipeline by identifying potential customers within your assigned territory (Charlotte, Florida, Texas).- Drive Sales Activities: Conduct face-to-face meetings, presentations, and product demonstrations to highlight Whip Around’s value proposition.- Close Deals: Collaborate with internal teams to manage the sales cycle and finalize contracts, earning commissions for closed deals.- Build Relationships: Foster strong, long-term relationships with prospects and customers to promote referrals and repeat business.- Track Sales Performance: Utilize provided tools and resources to monitor performance metrics and sales activities.- Stay Informed: Maintain a thorough understanding of Whip Around’s offerings and the competitive landscape to effectively address customer pain points. Requirements: • *What you’ll bring to the role:**- Proven experience in outside sales or a similar commission-based role.- Entrepreneurial mindset with a hunter’s mentality.- Exceptional communication, negotiation, and relationship-building skills.- Ability to manage time effectively and prioritize tasks in a remote, self-directed environment.- Confidence in handling objections and overcoming challenges.- Experience in fleet management or transportation sectors is a plus.We participate in E‑Verify and will verify employment eligibility via Form I‑9. The notice of E‑Verify Participation and Right to Work posters can be found here. Benefits: Apply tot his job Apply To this Job