Field Sales Representative

The Opportunity

Iceberg Cyber is building a high-performing field sales team in the Greater Toronto Area.

We are looking for an energetic, resilient B2B Field Sales Representative who already understands what it takes to start conversations with strangers, handle rejection, and create opportunities in person.

This is not a desk-based SDR role and it is not commission-only. You will receive a base salary, paid training, structured coaching, and a target commission opportunity.

Prior residential door-to-door sales experience is strongly preferred. We will also consider candidates with experience in fundraising, residential telecom, home improvement, roofing, windows, HVAC, pest control, security, landscaping, or other high-activity field-sales environments.

What you will do

You will have a defined territory across the GTA and create qualified business opportunities through face-to-face prospecting.

Your responsibilities will include:

• Visiting local businesses and speaking with owners, operators, and decision-makers.
• Creating approximately 15 planned field visits per day.
• Starting conversations with prospects who were not expecting a sales visit.
• Learning how the business currently handles its IT, cybersecurity, or technology needs.
• Identifying whether the business has an existing provider and when its contract may renew.
• Booking qualified introductory meetings.
• Following up on renewal dates and previously visited prospects.
• Keeping accurate notes, contact information, and follow-up dates in the CRM.
• Participating in daily coaching, role-play, and pipeline reviews.
• Communicating activity, results, obstacles, and opportunities clearly to the sales team.

What success looks like

In your first 90 days, you will:

• Become confident opening conversations with business owners.
• Build a repeatable territory and follow-up process.
• Consistently complete your planned field activity.
• Generate qualified appointments, not just names or conversations.
• Maintain accurate CRM records and renewal-date information.
• Demonstrate that you can learn from coaching and improve your results.

What we are looking for

The strongest candidates will have:

• Previous residential door-to-door sales, canvassing, fundraising, telecom, home-improvement, pest-control, security, or comparable field-sales experience.
• A record of personally generating conversations, appointments, or sales.
• Comfort working outdoors and moving throughout the GTA.
• Strong verbal communication and active listening skills.
• The ability to recover quickly from rejection.
• A competitive, disciplined, and coachable attitude.
• The ability to work independently without constant supervision.
• Reliable transportation.
• Availability to begin paid training within approximately two weeks.

You do not need previous cybersecurity or IT experience. You do need to be comfortable learning a business problem, asking thoughtful questions, and creating a clear next step.

Why join us

This is an opportunity to build a serious sales career from the field up.

You will receive:

• A real base salary instead of a commission-only arrangement.
• Direct coaching from experienced sales leaders.
• A defined territory and repeatable prospecting system.
• The chance to learn B2B sales, qualification, pipeline management, and technology solutions.
• A clear path to greater responsibility as the team grows.
• The autonomy and earning potential of field sales without being left to figure everything out alone.

Important reality of the role

This position is highly people-facing and activity-driven.

You should expect to:

• Spend most of the day in the field.
• Walk into businesses and start conversations.
• Hear “no” regularly.
• Work through uncertain or incomplete information.
• Track your activity carefully.
• Be measured on consistency, qualified opportunities, follow-up quality, and results.
• This role is not a fit for someone who wants an entirely remote job, prefers inbound leads only, or dislikes initiating conversations.