Most people hear "cold calling" and feel their soul leave their body.

If you're still reading, we should probably talk.

Who we are

Upsociate runs outbound sales for IT companies across North America (excluding Manitoba). These owners are excellent at keeping other people's businesses running and genuinely bad at filling their own calendar. We fix that for them.

What you'll actually do

Dial. A lot. About 100 to 150 calls a day.

Talk to business owners like a human being. That means being quick on your feet and genuinely conversational. The script keeps you pointed in the right direction. Where the call actually goes is on you.

Walk away from the call with a yes. Sometimes that's a 30 minute meeting between our client and the prospect. Sometimes it's just permission to send something over by email so we can stay in front of them. Both count as a win. No demos, no pitching, no closing.

Keep the CRM clean so we can all see what's working and what isn't.

What you don't have to do

You do not need to know what a firewall is. Seriously.

If a prospect asks something technical, your answer is "that's exactly what this meeting is for." You're setting the table, not cooking the dinner.

Who tends to do well here

You can get told no forty times before lunch and still sound genuinely pleasant at 2pm.





You're curious and genuinely interested in people. The best appointment setters ask better questions than they give answers.

Your English on the phone is clear and easy to follow.

You have reliable internet, a quiet space, and a headset that doesn't make you sound like a drive-thru speaker.

You take coaching well. We record calls and review them together.

Previous B2B phone experience and CRM familiarity are nice. Neither is a dealbreaker if you've got the personality and the work ethic.

The details

- Pay is $23/hour.
- Fully remote, work from home.
- Paid semi-monthly.

How to apply

Send us a short note telling us about the hardest thing you've ever had to sell, or the toughest conversation you've talked your way through. Two paragraphs is plenty. We're reading for how you write and how you think. Keep ChatGPT out of this one.

One more thing: start your application with the word Sasquatch. That's it, no explanation needed. If you dial a hundred numbers a day, details matter, and we'd rather find out now. If you skipped past this line, we'll know. So will Sasquatch.

Pay: $23.00 per hour

Benefits:

- Versatile schedule
- Work from home

Work Location: Remote

📌 Cold Caller /B Appointment Setter (Manitoba)
🏢 Upsociate
📍 Manitoba