Overview:

We are looking for competitive, coachable, and motivated salespeople who want to build experience in B2B field sales.

As a Field Sales Representative, you will visit predetermined local businesses, learn about their IT challenges, uncover their security vulnerabilities, and determine if they are actively looking to switch providers. The intelligence you gather becomes qualified opportunities we bring to our MSP partners. This is a field sales role with a base salary and performance-based commission, involving daily travel across the GTA and cold walk-ins to local businesses.

This opportunity is best suited for someone who is reliable, confident, competitive, and who thrives in fast-paced, performance-driven environments and wants earnings directly tied to results.

About Iceberg Cyber: Iceberg Cyber operates The Cyber Score, a lead generation service that connects small businesses with IT service providers through a proven door-to-door field sales outreach model. We physically walk into businesses and collect sales intelligence using our proprietary lead magnet, generating qualified leads for our MSP Partners.

Our field sales representatives visit 10–20 businesses per day, demonstrate security vulnerabilities, and identify which companies are actively ready to buy. We visit local businesses, uncover their IT and security gaps, and connect them with our MSP partners who are equipped to solve their problems.

Key Responsibilities: This position involves DAILY interactions with businesses. You will be visiting 10-20 predetermined businesses per day in your assigned territory Consistently follow a structured opening script and discuss the Cyber Score report with a representative at the business Ask diagnostic questions to identify their current IT setup, contract renewal dates, and pain points Navigate objections and discomfort with confidence without retreating Capture key intelligence points at every visit Be charismatic to build rapport quickly and adapt your approach based on the business Classify leads based on engagement and buying signals Log field notes immediately after each visit and follow-up details in HubSpot Maintain daily activity tracking and hit visit targets Work toward weekly and monthly sales targets Stay responsive and aligned with the scheduling and sales leadership teams Represent Iceberg Cyber and the Cyber Score professionally at all times

What We're Looking For:

Ideal Candidate: The ideal candidate is hungry, reliable, and results-driven. You may not have years of experience, but you are coachable, driven, and ready to build real skills in field sales. You are not afraid to drive, speak with businesses, handle objections, and be paid based on results.

Required: Must be 18+ and legally eligible to work in Canada Comfortable doing completely cold door-to-door walk-ins Valid Ontario driver’s licence Reliable personal vehicle Located in the GTA Comfortable with significant daily travel and a mobile workday throughout the GTA and surrounding Ontario markets based on business needs Comfortable talking about cybersecurity, IT services, and infrastructure after brief training Ability to follow a script and sales system consistently Strong communication skills and confidence speaking with local businesses At least one year of sales experience (preferably cold walk-in or door-to-door); in-home or field sales is an asset Ability to manage time independently and keep pace with a full schedule A competitive, self-motivated mindset and comfort working toward clear goals Coachable and willing to follow a proven process Comfortable working independently

Experience in any of the following is a strong asset: Automotive sales Telecom sales Home services sales Roofing, windows, HVAC, solar, alarms, pest control, or renovation sales Real estate or mortgage sales Fitness sales or membership sales Any commission-based sales environment Information technology or managed services HubSpot CRM

What's Covered Paid onboarding training plus ongoing weekly coaching Structured scripts, tools, training, and playbook are provided so you don't have to figure it out yourself Weekly predetermined and pre-researched businesses to visit Mileage and expense reimbursement A company provided tablet Growth opportunities within a rapidly expanding company A supportive, team-oriented environment where hard work is recognized and rewarded

What's Not Covered Commute to your first business of the day

Compensation This role includes a guaranteed base salary plus commission tied to results Base salary: $45,000/year + commission (OTE up to $100,000/year) Plus performance bonuses and incentives

Why Join Us Regular coaching, a company tablet, and a manager invested in your success Build real relationships with local business owners while helping them understand their security risks