Cold Caller / Appointment Setter – Real Estate Media (Full-Time, Canada Clients)

About Us
Check Yes Media is a real estate media company based in Toronto, Canada. We provide photography, video, 3D tours and floor plans for real estate agents and brokerages across the Greater Toronto Area. We're a small, fast-moving team and we're looking for a confident caller to help us grow.

The Role
You'll call real estate agents in the Toronto area. Your goal is to get them to book their first shoot with us. This is an outbound sales role: you'll make a high volume of calls every day, handle objections and turn interested agents into booked clients.

Responsibilities

• Make 100 outbound calls per day to real estate agents
• Pitch our services and book first shoots
• Follow up with interested leads by call and text
• Log all activity and lead status in our CRM (HubSpot)
• Hit weekly targets for conversations and booked shoots
• Join a weekly call review to keep improving

Requirements

• At least 1 year of cold calling experience with US or Canadian clients
• Excellent spoken English with a clear, natural accent
• Comfortable with rejection and confident handling objections
• Real estate or appointment-setting experience is a big plus
• Quiet workspace, reliable internet (25+ Mbps) and a backup connection
• A quality headset with a noise-cancelling mic
• Available to work the Eastern Time shift consistently

Tools You'll Use
Quo (phone system), HubSpot (CRM), Slack

Pay & Perks

• Base pay of $700–$1,000 USD/month, depending on experience
• A bonus for every first shoot you book, with no cap
• Paid bi-weekly via Wise
• Long-term role with room to grow as we scale

How to Apply
Only applications that follow these steps will be reviewed:

1. Use the subject line: "Booked Shoot – [Your Name]"
2. Tell us about your cold calling experience: which industry, which countries you called, and your best results (calls per day, meetings or sales booked).
3. Send a 1–2 minute video of yourself pitching a real estate photographer's services to an agent, as if you were on a cold call. Share it as a link (Loom, Google Drive or unlisted YouTube), and make sure the link is viewable.
4. Share your internet speed test screenshot.