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Entry Level Tech Sales Rep Jobs in Chicago, IL (NOW HIRING)

ALPHA MARKETING CONCEPTS INC

Be Seen First

(Entry Level) Business Sales Representative

Villa Park, IL · On-site

$45K - $65K/yr

Entry Level Business Representative Location: Chicago, IL Job Type: Full-Time | Entry Level If you ... technology solutions that fit their needs. No experience? No problem. We provide paid training ...

ALPHA MARKETING CONCEPTS INC

Be Seen First

(Entry Level) Business Sales Representative

Villa Park, IL · On-site

$45K - $65K/yr

Entry Level Business Representative Location: Chicago, IL Job Type: Full-Time | Entry Level If you ... technology solutions that fit their needs. No experience? No problem. We provide paid training ...

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All JobsTech Sales Rep JobsEntry Level Tech Sales Rep JobsEntry Level Tech Sales Rep Jobs in Chicago, IL

Entry Level Tech Sales Rep information

See Chicago, IL salary details

$29.9K

$65.4K

$103K

How much do entry level tech sales rep jobs pay per year?

As of Sep 1, 2026, the average yearly pay for entry level tech sales rep in Chicago, IL is $65,357.00, according to ZipRecruiter salary data. Most workers in this role earn between $48,400.00 and $77,800.00 per year, depending on experience, location, and employer.

What is an entry level tech sales rep?

An Entry Level Tech Sales Rep is a professional who is responsible for selling technology products or services, such as software, hardware, or IT solutions, typically to businesses or individual customers. They are often just starting their careers in sales and focus on generating leads, reaching out to potential clients, and supporting the sales process under the guidance of more experienced team members. Their role includes learning about the products, understanding customer needs, and helping to close sales while building foundational skills in technology sales.

What are the key skills and qualifications needed to thrive as an entry level tech sales rep?

To thrive as an Entry Level Tech Sales Rep, you need foundational knowledge of sales principles, strong communication abilities, and a basic understanding of technology, typically supported by a bachelor's degree or relevant experience. Familiarity with CRM software (such as Salesforce), email marketing tools, and common office productivity systems is often required. Persuasiveness, resilience, and active listening are important soft skills that help build relationships with clients and overcome objections. These competencies are crucial for achieving sales targets, fostering customer trust, and successfully navigating the fast-paced tech sales environment.

What are some common challenges entry level tech sales reps face during their initial months on the job?

Entry Level Tech Sales Reps often face challenges such as learning to effectively communicate complex technical products to clients who may have varying levels of technical knowledge. Adjusting to a fast-paced, target-driven environment can also be demanding, especially when balancing prospecting, follow-ups, and product training. Building a robust pipeline and overcoming initial rejection are common hurdles, but strong mentorship and teamwork can help new reps adapt quickly. Additionally, collaborating closely with senior sales professionals and technical teams provides valuable learning opportunities and support.

What is the difference between Entry Level Tech Sales Rep vs Technical Support Specialist?

AspectEntry Level Tech Sales RepTechnical Support Specialist
Required CredentialsHigh school diploma or equivalent; some roles prefer sales or technical certificationsHigh school diploma; technical certifications or relevant training often preferred
Work EnvironmentOffice setting, customer-facing, sales-focusedHelp desk, call center, or on-site support environment
Industry UsageCommon in tech companies, software firms, hardware providersCommon across IT, software, hardware, and telecom industries
Primary FocusSelling technical products and solutions to clientsDiagnosing and resolving technical issues for users

While both roles require technical knowledge and customer interaction, the Entry Level Tech Sales Rep focuses on selling tech products, whereas the Technical Support Specialist concentrates on troubleshooting and technical assistance. Your choice depends on whether you prefer sales and client engagement or technical problem-solving.

Entry Level Tech Sales Rep jobs near you
Infographic showing various Entry Level Tech Sales Rep job openings in Chicago, IL as of August 2026, with employment types broken down into 100% Full Time. Highlights an 75% In-person, and 25% Remote job distribution, with an average salary of $65,357 per year, or $31.4 per hour.

Sales Representative Entry-Level

True North Group LLC.

Merrillville, IN • On-site

Full-time

Medical, Life

Re-posted 14 days ago

Job description

Join Our Team at True North Group

Position: Sales Representative, Entry-Level

Number of Openings: 1 Territory Sales Position Available

About Us

At True North Group, we believe great careers are built on real relationships. We're a people-first supplemental insurance agency focused on helping small and mid-sized businesses protect what matters most: their families and employees. Whether you're just starting your professional journey or looking for a fresh start, this entry-level sales opportunity is the perfect launchpad. We'll give you the training, tools, and support to succeedno prior insurance experience needed.

The Role

As an Entry-Level Sales Representative, you'll get to know local businesses in your territory, learn about their employee benefit needs, and offer supplemental insurance plans that make a difference. You'll have the freedom to create your own schedule and work in a way that fits your clients' availabilitywhile being backed by a proven system and a supportive team.

Your job isn't just about making salesit's about making connections. You'll build trust, provide guidance, and become a valuable resource to the business owners and employees you serve.

What We're Looking For

A people-person who enjoys conversation and building relationships

Someone who's motivated, self-driven, and ready to learn

Great communicatorboth one-on-one and in front of a group

Strong organizational habits and attention to follow-up

A genuine desire to help others and make a positive impact

Willingness to obtain a Health & Life general lines license within 90 days (we'll help cover the cost later and provide study support)

Position Overview

This is an outside sales role, where you'll work locally in your own territory. You'll be trained to:

Visit businesses and introduce our supplemental insurance offerings

Meet with business owners and present to groups of employees (often 1050+ at a time)

Respond to client questions via phone and email

Set appointments, conduct follow-ups, and support clients through claims

Use our Salesforce CRM to track your activities, contacts, and progress

Work closely with your manager to set and meet sales goals

Build your own client base and develop long-term relationships

Share your weekly schedule and results with your manager

We Offer

Thorough Training: Get up to speed with both online and in-the-field coaching

Weekly Draw Pay: Steady income as you build your book of business, with bonuses and commissions available from day one

Exciting Incentives: Quarterly trips, cash bonuses, stock share awards, and lifetime-vested renewal commissions

Career Advancement: Clear pathways to grow into leadership, training, or higher-level sales roles based on your performance

Continued Development: Ongoing support to help you grow your skills and your confidence

Flexible Hours: You'll have the freedom to design your workday around your business clients' availability

Additional Qualifications

High school diploma required; a bachelor's degree or customer service experience is a plus

Strong work ethic and willingness to learn new skills

Comfortable using basic digital tools (email, calendar, CRM systems)

Already licensed in Health & Life, or ready to get licensed within 90 days

Start Your Career with Purpose

If you're ready to start a career that's flexible, meaningful, and full of opportunity, we'd love to meet you. At True North Group, we'll help you build something you can be proud ofone client and one conversation at a time.

Apply now and begin your journey with us today.

https://www.thetruenorthgroupllc.com