Outside Sales Representative

Job Title

Outside Sales Representative

Job Description

We are partnering with a fast-growing technology-driven company in the on-demand delivery and logistics industry to hire a freelance Outside Sales professional for the Illinois market. This role focuses on expanding restaurant and small business partnerships in and around Peru, IL, with an emphasis on emerging and rural markets. As an Outside Sales Associate, you will own a high-velocity, transactional sales cycle from initial outreach through close. You will spend the majority of your time in the field, meeting with local restaurant owners and decision-makers, presenting partnership opportunities, and negotiating commercial terms that support mutual growth.

Key Responsibilities:

• Prospect and qualify independent and regional restaurants within a defined territory centered near Peru, IL.
• Conduct in-person meetings with owners and key decision-makers to understand their needs and present tailored partnership solutions.
• Deliver clear, compelling sales presentations that articulate the value of joining a leading on-demand delivery marketplace.
• Manage a fast, transactional sales funnel, moving prospects from first contact to signed agreement within days.
• Negotiate core commercial terms (e.g., commission/revenue share, promotional structures) aligned with company guidelines.
• Leverage sales collateral, case studies, and performance data to build credibility and urgency.
• Maintain organized, accurate records of outreach, meetings, and deal stages in the designated tracking tools.
• Collaborate with a Regional Sales Manager to refine territory strategy, share competitive and market insights, and prioritize targets.

Travel & Territory: Field-based role covering Peru, IL and surrounding areas; candidates must reside within approximately 40 minutes of Peru, IL. Regular travel within roughly a 2-hour radius of the core territory, including rural and emerging markets. Occasional overnight stays and longer travel days may be required.

Compensation & Engagement: Employment Type: Freelance / Independent contractor-style engagement. Compensation Structure: Hourly base pay plus performance-based commission for each new partnership secured. Role Duration: Fixed-term contract, aligned to specific campaign dates and market expansion initiatives.

What We're Looking For:

• 2+ years of sales experience, preferably in a closing role selling to small or midsize businesses.
• Background in restaurant, food & beverage, hospitality, or local services is a strong plus.
• Comfort operating in a fast-paced, activity-driven sales environment with short deal cycles.
• Proven ability to prospect, self-manage a territory, and consistently hit or exceed targets.
• Strong communication, negotiation, and relationship-building skills with small business owners.
• Willingness and ability to travel extensively within the assigned territory.
• Self-starter mentality with an entrepreneurial, solution-oriented approach.

Additional Details:

• Location: Peru, Illinois and surrounding markets (field-based).
• Support: Access to sales enablement materials, market data, and guidance from an experienced sales leadership team.
• Start Date: Targeted to align with a specific market expansion window; exact dates provided during the interview process.

This freelance Outside Sales role is ideal for a motivated closer who thrives on building local business relationships, enjoys being on the road, and wants to help restaurants tap into a major on-demand delivery platform.