Cybersecurity Sales Specialist

Sterling Cybersecurity & Advisory Group · Windsor-Essex County, ON · Contract · Flexible/Part-time friendly

About Sterling

Sterling Cybersecurity & Advisory Group is a Canadian cybersecurity and compliance services firm serving small and mid-sized businesses across eleven industries in Canada and the US. Our slogan is "We're People First" and we mean it in both directions: we lead client conversations with education instead of fear tactics, and we build our team on transparency instead of vague promises.

About the role

We're adding two commission-based sales representatives in Windsor-Essex County. This is an independent contractor position designed with flexibility at its core: you control your schedule, you decide how you work, and the role fits alongside existing work, studies, or other commitments. It's built to start as a supplementary income stream and for those with the drive, to grow into a full-time career. Year one is building season; what you build keeps paying.

What you'll do

You'll identify and connect with small and mid-sized businesses that need cybersecurity and compliance support, guide them through an education-first sales conversation, and bring them onto Sterling's services - endpoint protection, managed security (SOC as a Service), security training and SIEM. You'll manage your pipeline in our purpose-built CRM, which maps out your daily activities based on where each prospect sits, and you'll work directly with our Chief Growth Officer through onboarding and weekly coaching.

How you're paid

This is a 100% commission structure with two earning streams: one-time commissions on annual product sales, and monthly residuals on managed service clients — meaning clients you bring onto our monthly service pay you every month they stay, for as long as they stay. Your income compounds as your client book grows: the work you do in year one can continue paying in years two, three, and beyond, stacking on top of new sales. Earnings are uncapped. We'll walk every serious candidate through the actual commission model and the math behind it during the interview process.

What we provide

Full onboarding and training from zero - cybersecurity experience is not required. You'll get our call frameworks, objection-handling training built on a proven methodology, industry-specific pitch materials across our eleven verticals, a CRM that tells you exactly what to do each day, and weekly coaching directly from sales leadership.

Who thrives here

Self-starters who treat their pipeline like a business. Relationship-builders who'd rather educate than pressure. People patient enough to build an asset instead of chasing a paycheque - and hungry enough to turn it into a career. Based in or near Windsor-Essex County, comfortable prospecting by phone, email, and in person.

Location advantage

Windsor-Essex sits on one of the busiest commercial border crossings in North America.

How to apply

Apply here, or message Devin Garganta directly on LinkedIn. We read every application, and every serious candidate gets a real conversation - with the person, not just the résumé.

Sterling Cybersecurity & Advisory Group

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Cybersecurity Sales Specialist