Entry Level Insurance Sales Jobs in Illinois (NOW HIRING)

Entry-Level Sales

Reports To: Director of Training

Location: Chicago, IL

Environment: Onsite

Status: Non-Exempt; Salaried

Who We Are:

Recognized by Gartner in their Modern 4PL Market Guide, Redwood Logistics is at the forefront of industry innovation. Our cutting-edge supply chain technology pairs with the expertise of our brilliant minds to empower logistics execution across North America and Mexico.

Leveraging a comprehensive range of services, data-centric network solutions, and a seamlessly integrated platform, we have established our prominence as a key player in the mid-market segment within the freight tech industry.

Whether you’re just starting your career or are an established professional looking for your next opportunity, Redwood inspires innovation across teams to provide transformative solutions for our customers.

Are you ambitious, competitive, and eager to build a lucrative career in sales? We are looking for an energetic Entry-Level Sales Representative to join our fast-paced sales team!

In this role, you will learn the ins and outs of our industry, build strong negotiation skills, and develop business relationships from the ground up. You don't need years of corporate experience to succeed here—we provide the training, tools, and continuous mentorship you need to thrive. If you have grit, a high energy level, and a desire to control your own earning potential, we want to hear from you.

• Build Your Pipeline: Proactively reach out to potential prospective clients/partners via cold calling, email, and networking to generate new business.

• Negotiate & Close: Learn to negotiate competitive market rates and close sales opportunities in a fast-paced environment.

• Manage Relationships: Serve as a trusted point of contact for your account portfolio, ensuring exceptional service and ongoing business growth.

• Collaborate: Partner closely with internal teams to streamline operations and ensure seamless service delivery.

• Hit Goals: Work toward clear, achievable daily activity metrics and monthly sales goals.

• No prior sales experience required! A Bachelor’s degree, Associate's degree, or equivalent hands-on customer service/work experience is preferred.

• Strong communication skills and a confident, professional telephone presence.

• High motivation, resilience, and a coachable mindset—you thrive on feedback and continuous learning.

• Ability to multitask, problem-solve on the fly, and manage your time effectively in a dynamic environment.

What We Offer:

• Access to experts and resources for your Learning & Development journey
• Opportunity for internal mobility
• Employee referral bonus program
• Employee Resource Groups (ERGs)
• Annual fundraising and volunteer events to give back to communities
• Paid time off, floating holidays, time off to volunteer and rollover
• Paid parental leave
• Medical, dental, vision and 401k plans (with match)
• Flexible spending account, mass transit and dependent care plans available
• Health savings account, with a annual company contribution for plan participants
• Short-term and long-term disability; life insurance policies subsidized by company
• Additional benefits including pet insurance, accident care, access to legal advice and more

Work Schedule:

This is a full-time position with a hybrid schedule following completion of our training program.

Team members work onsite Monday through Friday during the initial training pod period. After successfully graduating from training, the schedule transitions to four days in the office and one remote workday each week.

Standard hours are 7:00 AM – 4:00 PM or 8:00 AM – 5:00 PM with a one-hour break. Additional flexibility may be available based on team coverage needs

Compensation Range:

$45,000 - 50,000 + Established, long-standing commission structure with high upside

This position is eligible to earn monthly commission incentives based on individual and company performance. On-Target Earnings (OTE): $100-150K+ on average for established reps.

The estimated pay range reflects an anticipated range for this position. The actual base salary offered will depend on a variety of factors, including the qualifications of the individual applicant for the position, years of relevant experience, specific and unique skills, level of education attained, certifications or other professional licenses held, the geographical location in which the applicant lives and/or which they will be performing the job, and the budgeted funds for this role.

Redwood is an equal opportunity employer. Employment decisions at the Company are based on individual merit, qualifications, abilities, and the Company’s needs and resources. The Company does not discriminate in recruiting, hiring, compensation, promotions, discipline, termination or any other aspect of employment on the basis of an individual’s actual or perceived race, color, creed, religion, sex (including pregnancy, childbirth and related medical conditions), sexual orientation, gender identity, national origin, ancestry, citizenship status, age, disability, marital status, military service or status, genetic information, arrest and conviction record, credit history, or any other basis protected by applicable law.

Click Apply below to submit your resume! We look forward to reviewing your application.