Outside Sales Representative (1099 Contractor)

Who is Whip Around?

Whip Around was born in 2016, originally to help freight companies in New Zealand tackle their paper-based compliance burden. It was whilst working for some of the globe’s largest freight companies, that we saw first-hand how much time paper was costing fleet managers every day. Within a year, the US market was calling loudly as Whip Around met a clear pain point for businesses with fleets.  Whip Around now services customers from coast to coast in the US and around the world.

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.

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 .