B2B Logistics Sales Representative

Company: Ristasko Logistics LLC
Location: Chicago, IL
Company Headquarters: Dallas, TX
Job Type: Independent Contractor (1099)
Compensation: $50,000 annualized base + competitive commissions + performance-based bonuses

About Ristasko Logistics LLC

Ristasko Logistics LLC is a Dallas, Texas-based company specializing in shipping, logistics, and business solutions that help companies reduce costs, streamline operations, and improve efficiency.

As part of our continued growth, we are expanding into the Chicago market and building out our Chicago sales office. We are looking for an experienced, motivated B2B Sales Representative to help establish our presence, develop new business relationships, and drive sales growth throughout the region.

This is an exciting opportunity to join a growing company at an early stage of its Chicago expansion and play a meaningful role in developing a new market.

While our primary focus is shipping and logistics, we also offer additional business solutions, including software, website development, digital marketing, and other services.

About the Opportunity

We are seeking a driven, entrepreneurial sales professional with experience in B2B shipping, logistics, or transportation sales.

Candidates with backgrounds at UPS, FedEx, Unishippers, DHL, or similar shipping and logistics organizations are especially encouraged to apply.

The ideal candidate understands the challenges businesses face with shipping costs, carrier relationships, and logistics operations. You should be comfortable developing new business, building relationships with decision-makers, and managing the full sales cycle.

As an early member of our Chicago sales expansion, you'll have the opportunity to help shape our local sales strategy, establish a customer base, and contribute directly to the growth of our Chicago operations.

This independent contractor position offers a $50,000 annualized base, a competitive commission structure, and performance-based bonuses, with final terms depending on experience.

Key Responsibilities

Business Development & Sales

• Identify and pursue new B2B sales opportunities throughout Chicago and surrounding markets.
• Help establish and expand Ristasko Logistics LLC's presence in the Chicago business community.
• Develop relationships with business owners, operations managers, shipping departments, and key decision-makers.
• Generate leads through networking, referrals, cold outreach, and existing business relationships.
• Analyze prospective customers' shipping needs and identify opportunities for cost savings and operational improvements.
• Present competitive shipping and logistics solutions tailored to individual business needs.
• Manage the complete sales cycle, from prospecting and qualification to negotiation and closing.
• Maintain a strong pipeline of qualified business opportunities.
• Build long-term customer relationships to generate recurring business and referrals.
• Contribute ideas and market insights to help develop our growing Chicago sales operation.

Additional Business Solutions (Optional)

• Identify opportunities to introduce complementary business services, including software solutions, website development, and digital marketing.
• Cross-sell additional services to existing and prospective logistics clients.
• Collaborate with the broader team to offer comprehensive solutions to business customers.

Qualifications

Preferred Experience

• Previous B2B sales experience, preferably in shipping, logistics, transportation, or related industries.
• Experience working with UPS, FedEx, Unishippers, DHL, freight brokerages, or similar companies is highly desirable.
• Understanding of parcel shipping, commercial shipping rates, carrier services, and logistics solutions.
• Proven ability to prospect, build relationships, and close new business.
• Existing business relationships or a strong professional network in the Chicago market is a major plus.

Skills & Attributes

• Excellent communication, negotiation, and relationship-building skills.
• Self-motivated, organized, and results-oriented.
• Entrepreneurial mindset and enthusiasm for helping establish a new sales market.
• Ability to independently manage sales opportunities and maintain strong client relationships.
• Confidence working directly with business owners and senior decision-makers.
• Experience with CRM systems and sales prospecting tools.
• Strong initiative, accountability, and commitment to results.

Additional Skills That Are a Plus

• Experience selling software, SaaS, or technology solutions.
• Understanding of website development, digital marketing, SEO, or other business services.
• Experience cross-selling multiple business solutions.

Experience in digital services is not required. A strong background in logistics and B2B sales is our primary priority.

Compensation & Opportunity

• $50,000 annualized base contract compensation.
• Competitive commissions with significant earning potential.
• Additional performance-based bonuses.
• Commission and bonus structure tailored to experience and performance.
• Opportunities to earn additional commissions through complementary business services.
• Opportunity to become an important part of our Chicago market expansion.
• Potential for increased responsibilities as the Chicago sales operation grows.
• Flexibility and independence associated with an independent contractor arrangement.
• Long-term growth potential within an expanding company.

Final compensation and commission terms will be outlined in the independent contractor agreement.

Who We're Looking For

We're looking for more than someone who can sell. We want an experienced professional who is excited about helping build something.

Perhaps you've worked at UPS, FedEx, Unishippers, or another logistics provider and have built a strong understanding of the industry, customer relationships, and the Chicago market.

You know how to open doors, identify opportunities, negotiate deals, and build long-term partnerships.

With our headquarters established in Dallas and our expansion underway in Chicago, this is an opportunity to become an important part of a growing sales operation from the beginning.

If you're entrepreneurial, motivated by competitive commissions, and excited about helping grow a business in the Chicago market, we'd love to connect.

Pay: From $50,000.00 per year

Benefits:

• Paid time off

Work Location: Hybrid remote in Chicago, IL 60617