Outside Sales Representative in Chicago – Build Your Empire, Not Just a Pipeline

Are you a hunter, not a farmer? Do you thrive on the thrill of the chase and the satisfaction of closing a major deal? Apex Growth Partners, a leader in innovative B2B solutions, is seeking a tenacious Outside Sales Representative to dominate the Chicago territory. This isn’t just a sales job; it’s a career-building opportunity where your drive directly fuels your income and our collective growth. If you’re ready to trade a desk for the road and a salary for uncapped earnings, we want to talk to you.

About the Role: Your Territory, Your Fortune

As an Outside Sales Representative, you will be the frontline revenue driver for Apex Growth Partners in the greater Chicago metropolitan area. You will own your territory, identifying and engaging new business prospects while expanding relationships with our existing client base. Your mission is to understand client pain points, craft compelling solutions using our industry-leading product suite, and negotiate contracts that deliver exceptional value. You will collaborate closely with our marketing and customer success teams but will ultimately be the captain of your sales destiny, managing the full cycle from prospecting to close.

What You’ll Do:

• Generate new business through proactive prospecting via cold calling, networking events, and strategic market research.
• Conduct on-site client meetings and product demonstrations to showcase ROI.
• Develop and execute a quarterly territory business plan to exceed sales quotas.
• Negotiate and finalize complex B2B sales agreements.
• Maintain accurate forecasts and pipeline data in our CRM (Salesforce).
• Provide market feedback to product and marketing teams.

Requirements: The Hunter’s Profile

We are looking for a self-starter with a proven track record in B2B outside sales. You must be resilient, coachable, and possess an unwavering commitment to excellence.

Essential Experience & Skills:

• 2+ years of successful outside/B2B sales experience, with a consistent record of meeting or exceeding quota.
• Proven ability to cold call, prospect, and build a pipeline from scratch.
• Strong negotiation and closing skills; you can handle objections and turn “no” into “yes.”
• Excellent verbal and written communication skills; you are a confident presenter.
• Valid driver’s license and reliable transportation; you will be traveling within the territory.
• Proficiency with CRM software and Microsoft Office Suite.
• A bachelor’s degree is preferred but not required if you have equivalent experience and results.

Compensation & Benefits: Your Success is Our Success

We offer a competitive, performance-driven compensation package designed to reward top performers handsomely.

Salary Range:

Base Salary: $50,000 – $65,000 USD/year (commensurate with experience)

Plus an uncapped commission structure with accelerators. On-Target Earnings (OTE) for a strong performer in this role range from $85,000 to $100,000+ USD/year. Top performers consistently earn well beyond $120,000.

Comprehensive Benefits Package Includes:

• Health & Wellness: Medical, dental, and vision insurance (90% employer-paid for employee-only coverage).
• Financial Security: 401(k) plan with company match.
• Work-Life Balance: Generous Paid Time Off (PTO) and company holidays.
• Tools for Success: Company-provided laptop, CRM, and a monthly car allowance ($500) plus mileage reimbursement.
• Growth: Continuous training, mentorship from senior sales leaders, and clear paths for advancement into sales management or strategic roles.
• Culture: A collaborative, competitive, and fun team environment with regular outings and recognition events.

How to Succeed at Apex Growth Partners

The ideal candidate is a motivated, curious, and persistent professional who loves the autonomy of outside sales. You are a strategic thinker who plans your week but can pivot on a dime. You build genuine rapport quickly and are consultative, not pushy. You are data-driven, using your CRM to inform your strategy, and you are accountable for your results. If you are looking for a company that will invest in you, provide a superior product to sell, and give you the freedom to build a lucrative career, you have found it.

This is a full-time, exempt position based in the Chicago territory. Apex Growth Partners is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.

Ready to take ownership of your income and territory? We look forward to reviewing your background and accomplishments.