Technical Geek Jobs (NOW HIRING)

Company Description

Geek Heros is a veteran- and first responder-owned technology company based in the Greater Chicago area. We help professional service businesses, medical organizations, and growing companies use technology to operate more securely, efficiently, and competitively.

Our core services include fully managed IT, 24/7 helpdesk support, cybersecurity strategy and monitoring, cloud migration, network design, disaster recovery, compliance-focused infrastructure, and proactive maintenance. We also offer practical AI solutions designed to help businesses automate workflows, improve client communication, and increase productivity. Website design and development services remain available for select clients, although they are not our primary focus.

Geek Heros serves clients locally and across the United States with responsive support and technology solutions tailored to real business needs.

Role Description

Geek Heros is seeking a motivated, independent Commission-Only Technology Sales Representative to grow our client base. This is a full-time, on-site role based in Arlington Heights, Illinois, structured as an independent contractor position rather than a W-2 employee role.

You will identify, qualify, and develop relationships with prospective clients, including medical practices, professional service firms, and other businesses that can benefit from managed IT, cybersecurity, AI automation, and related technology solutions. You will conduct discovery calls, schedule and attend virtual or in-person meetings, present solutions, prepare proposals, and follow up consistently to move opportunities through the sales process.

This role is designed for a self-starter who is confident prospecting and building a pipeline. Compensation is commission-only at the start, with high commission potential intended to reward strong performance. Successful representatives who demonstrate consistent results may have the opportunity to transition into a competitive paid sales position with base compensation plus commission.

Responsibilities

• Prospect, qualify, and build relationships with new business clients.
• Present managed IT, cybersecurity, AI, and technology solutions in clear, business-focused language.
• Conduct discovery calls to identify operational, security, compliance, and growth needs.
• Schedule and attend client meetings, both virtually and in person.
• Prepare proposals, quotes, and solution recommendations with support from technical and operations teams.
• Maintain accurate activity, pipeline, and opportunity records in the company CRM.
• Consistently follow up with prospects and guide opportunities through the sales cycle.
• Meet or exceed agreed-upon sales activity and revenue goals.
• Represent Geek Heros at networking events, professional gatherings, and community opportunities.
• Build long-term relationships that create repeat business and referrals.

Compensation

This is a 1099 independent contractor, commission-only position. There is no base salary at the start; however, Geek Heros offers substantial commission opportunities designed to reward successful sales performance.

Top-performing representatives may be considered for advancement into a competitive compensated sales role that includes a base pay structure plus commission, depending on performance, business growth, and company needs.

Qualifications

• Strong consultative sales, prospecting, and relationship-building abilities.
• Experience managing a sales cycle from outreach and discovery through closing.
• Ability to explain IT, cybersecurity, AI, and other technical services to non-technical decision-makers.
• Comfortable generating leads, making outbound calls, networking, and creating opportunities independently.
• Strong communication, presentation, organization, and follow-up skills.
• Experience using CRM platforms, email, spreadsheets, and presentation tools.
• Comfortable meeting clients in person and participating in professional networking events.
• Sales experience in managed IT services, SaaS, cybersecurity, AI solutions, medical technology, professional services, or business-to-business sales is strongly preferred.
• Existing relationships with medical practices, professional services firms, business owners, or local organizations are a plus.
• Willingness to learn Geek Heros’ services, evolving cybersecurity practices, AI offerings, and client industries.