Inside Sales Representative (Entry Level)

Looking for more than just a job? At Circle, you’ll find a fast-paced, high-energy environment where motivated people build real careers. If you’re competitive, coachable, and excited to learn how sales really works, this is your opportunity to get in early and grow fast.

Why Circle?

• Real career growth with clear advancement paths—we promote from within
• High-energy, team-first culture where wins are celebrated and collaboration matters
• Competitive pay + uncapped commission so your effort directly impacts your earnings
• Dog-friendly Chicago office with team events, outings, and a supportive environment

👉 Want to see it for yourself?

Explore what it’s like to work at our Chicago office:

https://careers.circledelivers.com/account-executive-chicago

About Us

Circle is a rapidly growing third-party logistics (3PL) company supporting businesses across the U.S. 24/7. What started as a small entrepreneurial venture has grown into a nationwide team of 500+ people—and we’re just getting started.

Day in the Life at Circle

No two days are exactly the same—but here’s what a typical day in our Chicago office might look like:

• Kick off the day with coffee, team huddles, and goal-setting
• Connect with potential customers through phone calls and email outreach
• Learn how to qualify leads, handle objections, and build lasting relationships
• Work closely with teammates and managers to solve real customer challenges
• Track progress and wins in CRM tools
• Celebrate milestones, call blocks, and closed deals together as a team

The Role

As an Inside Sales Representative, you’ll learn the fundamentals of sales while helping drive new business for Circle. You’ll receive hands-on training, daily coaching, and clear performance goals designed to help you grow quickly.

No prior sales experience required—we hire for attitude, work ethic, and coachability.

What You’ll Be Responsible For

• Prospect and qualify new customers through outbound calls and emails
• Research potential clients using tools like Google and ZoomInfo
• Build and maintain relationships with new and existing accounts
• Collaborate with internal teams to ensure excellent service
• Track daily activity and progress in CRM systems
• Learn how to manage and grow accounts over time

What We’re Looking For

• Motivated, competitive, and goal-oriented mindset
• Comfortable communicating by phone and email
• Coachable and open to feedback
• Reliable, professional, and team-focused
• Interest in sales, business, or entrepreneurship

Performance Expectations (We’ll Coach You Here)

• Make outbound calls daily to build pipeline and confidence
• Hit activity and performance goals with manager support
• Maintain a service-first, solutions-focused mindset
• Show up consistently with integrity and accountability

Compensation & Benefits

• $50,000 base + uncapped commission
• Paid holidays and PTO after 90 days
• Health, dental, and vision insurance
• 401(k) retirement plan
• Ongoing sales training and career development
• Dog-friendly office

Your Growth Path

Top performers can grow into roles such as

• Senior Sales Representative
• Account Executive
• Sales Manager
• Leadership and strategic roles

Advancement is based on performance—not tenure.

Ready to Launch Your Career?

If you’re driven, eager to learn, and excited to build something meaningful, we’d love to meet you.

Apply today and start your sales career with Circle.