Pay Range $70,000 – $120,000
Full-Time | Base + Uncapped Commission
Are you a relentless “Hunter” who thrives on closing deals and building a book of business? ITRegulators, a growing Managed Service Provider (MSP) serving the Chicagoland area, is looking for a high-energy Sales Executive to spearhead our market expansion.
We provide strategic technology partnerships that help businesses stay secure and efficient. You will be responsible for identifying small-to-medium business (SMB) opportunities, navigating the “C-Suite” conversation, and securing long-term managed service contracts.
What’s in it for You?
- Aggressive Commission Structure: We offer a lucrative “First Month’s Revenue” bonus on every new managed services contract you sign.
- Residual Income: We reward long-term thinking. You’ll earn a monthly percentage of the accounts you manage for as long as they stay with us.
- Growth Opportunity: Join us during a pivotal growth phase. You will have a direct seat at the table as we scale our sales operations.
- Proven Stability: Sell with confidence, knowing you are backed by a team with a long-standing reputation for technical excellence in the local market.
Responsibilities
- Lead Generation: Aggressively prospect via cold calling, networking, and LinkedIn to build a robust sales pipeline.
- The “Discovery”: Conduct initial meetings to identify pain points in a prospect’s current IT, security, and cloud environment.
- Consultative Closing: Present tailored IT solutions and close monthly recurring revenue (MRR) contracts.
- Relationship Management: Maintain the “high-touch” relationship during the onboarding phase to ensure client satisfaction and identify upsell opportunities.
Requirements
- Experience: 3–5 years of B2B sales experience (Background in Technology, SaaS, or Managed Services is highly preferred).
- Mindset: A “Hunter” mentality. You are self-motivated, resilient, and driven by hitting (and exceeding) targets.
- Communication: Ability to translate technical concepts into business value for business owners and executives.
- Local Presence: Deep knowledge of the Chicagoland business landscape and a willingness to be “feet on the street” when necessary.
What We Offer (Compensation & Benefits)
First Year Pay Forecast: $100,000+
Clean and transparent earning potential. We offer a competitive base salary (depending on experience) plus uncapped commission and bonuses tied to meeting or exceeding sales quotas.
- Comprehensive benefits package (Health, Dental, and Retirement plans).
- Clear pathways for professional growth and leadership advancement within the company.
- A collaborative, high-energy, and dynamic work environment.
How to Apply
If you are driven, enthusiastic, and ready to make a significant impact in the IT industry, we want to hear from you! Please submit your resume and a brief cover letter explaining your relevant sales experience and why you are the ideal fit for ITRegulators, Inc.
Join us at ITRegulators, Inc. as we embark on an exciting journey to elevate our company and deliver exceptional IT solutions to our clients in 2026 and beyond!