Outside Sales Representative (1099 Contractor)

Whip Around; Town of Texas (WI); Remote; USD 50,000 - 80,000; Full time

Job summary

A dynamic company is seeking an Outside Sales Representative to join their team as a 1099 contractor. This role offers flexibility and the opportunity to drive new business in a commission-based environment. Ideal candidates are motivated, entrepreneurial, and excel in relationship-building to demonstrate value and close sales with small to mid-sized businesses. Responsibilities include managing the sales cycle, conducting presentations, and maintaining long-term customer relationships.

Qualifications

• Proven experience in outside sales or similar commission-based roles.
• Entrepreneurial mindset with a proactive, 'hunter' approach.

Responsibilities

• Identify and target prospects within your territory.
• Conduct face-to-face meetings and product demonstrations.
• Manage the sales cycle and close deals to earn commissions.

Skills

Communication

Negotiation

Relationship Building

Time Management

Job description

Outside Sales Representative (1099 Contractor)

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Who is Whip Around?
Whip Around was founded in 2016 to help freight companies in New Zealand manage their paper-based compliance. Working with some of the largest freight companies worldwide, we recognized the significant time and cost associated with paperwork for fleet managers. As demand grew, we expanded into the US market, addressing the needs of fleet-related businesses across the country. Today, Whip Around serves customers coast to coast in the US and globally.

Role Overview:
As a 1099 Outside Sales Representative, you will operate as an independent contractor tasked with generating new business within your designated territory. This commission-based position is ideal for motivated, entrepreneurial individuals who excel in a high-energy, goal-oriented environment.

In this role, you'll have the flexibility to set your own schedule and income potential, representing a cutting-edge fleet management solution. You will be responsible for your own expenses, including transportation, communication, and equipment. Your focus will be on building relationships, demonstrating Whip Around’s value, and closing sales with small to mid-sized businesses.

• Identify and target prospects within your territory (Charlotte, Florida, Texas).
• Conduct face-to-face meetings, presentations, and product demonstrations.
• Manage the sales cycle and close deals to earn commissions.
• Develop and maintain long-term customer relationships.
• Use provided tools to monitor performance metrics and sales activities.
• Stay informed about Whip Around’s products and the competitive landscape.

Requirements:

• Proven experience in outside sales or similar commission-based roles.
• Entrepreneurial mindset with a proactive, 'hunter' approach.
• Excellent communication, negotiation, and relationship-building skills.
• Ability to manage time effectively in a remote, self-directed environment.
• Confidence in handling objections and overcoming challenges.
• Experience in fleet management or transportation sectors is a plus.

Additional Details:

• Seniority level: Entry level
• Employment type: Contract
• Industry: IT Services and IT Consulting