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Sales Development Representative (Remote Chicagoland Area)

June 13, 2026

Pay: $18 per hour plus uncapped commissions (OTE ~$75,000 - $250k annually) About Extrity Services At Extrity Services, we redefine security by placing a premium on emotional intelligence, de-escalation, and cultivating a thriving company culture. We believe that security goes beyond physical safety; it's about creating an environment where everyone feels secure and valued. We are the leading provider of unarmed and armed security solutions; we pride ourselves on delivering top-notch, reliable services to a wide range of clients. Our commitment to operational excellence, stringent standards, and meticulous attention to detail is what sets us apart from the competition. Join us at Extrity Services, where security is a collaborative effort that values emotional intelligence, embraces de-escalation techniques, and celebrates the unique culture of each client. Together, let's redefine what it means to feel secure. Job Description As a Sales Development Representative at Extrity Services, you will be a key driver of company growth by generating new business opportunities and developing strong relationships across industries including healthcare, hospitality, cannabis, education, luxury retail, and residential communities. This role is designed for motivated, performance-driven sales professionals who thrive in a commission-only environment and are eager to scale their earnings through results. You will promote both security services and de-escalation training solutions while upholding Extrity Services’ commitment to professionalism, integrity, and service excellence. This position is remote within the Chicagoland area. What You’ll Be Doing <ul><li>Generate and qualify new business leads using Seamless AI and LinkedIn Sales Navigator</li><li>Manage and track all sales activity within HubSpot CRM</li><li>Conduct outbound outreach and follow-ups within a 30-day sales cycle</li><li>Attend monthly in-person travel engagements to meet prospective clients</li><li>Promote de-escalation seminars in conjunction with security service offerings</li><li>Partner with Operations to ensure smooth and timely client onboarding</li><li>Achieve a monthly minimum target of 20 qualified sales opportunities</li><li>Participate in weekly sales meetings and role-playing exercises</li><li>Maintain clear, professional communication through Slack and internal tools</li><li>Leverage sales technology including HubSpot, Seamless AI, Excel, and Slack </li></ul>What You’ll Bring <ul><li>Minimum of 2 years of sales experience (professional services or security industry strongly preferred)</li><li>Demonstrated ability to close deals of varying size and complexity</li><li>Strong verbal and written communication skills</li><li>Proficiency with CRM platforms, particularly HubSpot</li><li>Experience using LinkedIn Sales Navigator and lead-generation tools</li><li>Highly self-motivated with a results-driven mindset</li><li>Ability to adapt to evolving market conditions and feedback</li><li>Existing relationships within security industry (preferred)</li><li>Bachelor’s degree (preferred, not required) </li></ul>Compensation & On-Target Earnings (OTE) This role is $18 per hour plus commission, with monthly commission payouts and a structured tier system that rewards performance and revenue generation. Earnings increase as revenue milestones are achieved. There is no cap on commissions, and top performers are rewarded with accelerated earning potential and long-term growth opportunities. Why Join Us At Extrity Services, you’re not just selling a service—you’re helping organizations create safer, more respectful environments. This role offers high earning potential, professional development, and the opportunity to build a long-term career within a rapidly growing company. Our Approach Emotional Intelligence - We lead with empathy. Our professionals are trained to understand emotional dynamics and respond thoughtfully in every interaction. De-escalation Mastery - We specialize in resolving tense situations through calm, strategic responses that prioritize safety and dignity. Culture as a Foundation - Security is an extension of organizational culture. Our solutions integrate seamlessly with client values to foster secure and harmonious environments. Diversity, Equity & Inclusion Extrity Services is an equal opportunity and affirmative action employer. We celebrate diversity and do not discriminate based on race, religion, color, national origin, gender (including pregnancy, childbirth, or related conditions), sexual orientation, gender identity or expression, age, veteran status, disability, or any other legally protected characteristic.

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...