Business Development Rep — CalgaryWestern Rockies IT
Read this if you like talking to strangers, you have something to prove, and you would rather knock on five doors than open one inbox.
Who we are
Western Rockies IT helps businesses work smarter through our BusinessOS framework — mapping workflows, eliminating friction, and building AI automations that give your team time back for the work that actually matters. That is how we open doors. Once we are inside, we become the full-service IT partner behind the scenes — managing technology, cybersecurity, Microsoft 365, and everything in between for around 80 businesses across Calgary, Edmonton, and Fernie. We have been doing this since 1991. We are not a sleepy MSP.
The opportunity
Calgary is full of 15 to 200-person businesses running on duct tape and a part-time IT guy named Steve. They know it. They want to fix it. They just have not met us yet.
That is your job — get them to meet us.
What you will actually do
Build target lists from systems like Apollo or your preferred mass list application, and work them like you mean it. Pick up the phone. A lot. Cold calls are not dead — they are just done badly by most people. Run email sequences that read like a human wrote them. Use LinkedIn for actual selling, not for posting motivational quotes. Qualify leads against real MSP fit criteria — not vibes. Run discovery calls and demos with business owners. Close deals up to roughly $5K MRR on your own — bigger or messier ones get handed to senior leadership and you stay on the deal. As we grow this roll, you’ll be given larger scope and latitude. Keep the CRM like HubSpot or Pipedrive clean so the rest of us are not chasing your notes. Tell us every week what is working, what is not, and what you need.
What success looks like in your first year
You consistently hit qualified pipeline and MQL targets. Your MQL-to-discovery conversion is one we can point at and brag about. You have closed a stack of smaller deals end-to-end. Your CRM is so tidy people use it as a reference. When someone in Calgary's SMB scene says "we should call an IT company," your name comes up.
What you bring
You NEED to be in Calgary. This is not a remote work from another city job.
You need 3 to 5 years of B2B sales — and you can point at specific deals you won and why. Exceptional verbal communication. You can land a clear, confident message on a 30-second cold call to a business owner who was not expecting you. Native-level English fluency, spoken and written — our prospects are Calgary SMB owners and operators, and first impressions are the whole game. You are not afraid of the phone. You actually prefer it. Apollo, Pipedrive, Hubspot or equivalent — you have used real sales tools. LinkedIn social selling that goes beyond a polished profile. You live in Calgary and you like being in the field. Valid driver's license and a vehicle that starts in February.
You understand AI at a working level — not as a developer, but as someone who can hold an intelligent conversation about automation, large language models, and what they actually do for a business. Curiosity about the space is the floor. Hands-on experience with AI tools is a real advantage. This matters because AI and BusinessOS is how we open doors in Calgary — and you need to believe in what you are selling.
Bonus points if
You have sold MSP, IT services, or B2B tech before. You have sold to SMB owners directly — the person whose name is on the door. You can hold your own in a conversation about Microsoft 365 or cybersecurity. Your last job shows real progression, not just tenure.
What you get from us
Closing authority after proven competence — we need to know who you are and build the trust. The faster we get there, the faster you can close on your own. This is not a permanent farm role. A territory full of warm prospects and a real ICP to work against. A promotion path based on results, not on waiting your turn. A modern tool stack — Apollo, Pipedrive, Hubspot, and automation we build ourselves. A differentiated pitch through BusinessOS and our AI services practice — people actually want to talk to us about this one, and we will talk about it a lot. Direct access to the President and senior leadership — we are not a place where good ideas die in a Slack channel.
What this job is
This is a hybrid role. You will be in the field meeting prospects, at home running sequences and calls, and occasionally in the office collaborating with the team. If you are looking for fully remote, this is not it. If you are looking for a desk job, this is also not it. Field presence in Calgary matters — that is the whole point.
What this job is not
A place to coast. A slow-moving corporate sales role with a six-month ramp. A spot for someone who needs a script for every conversation.
How to apply
Apply on this posting. Send your resume and a short note — no more than fifteen sentences, on the best deal you ever closed. What it took, what you learned, what you would do differently. Keep it tight. If you send more than that, you did not understand the assignment.
If we are interested, we will ask you for an initial interview where you will be asked to cold pitch one of our team on a product of your choosing. We are not testing your product knowledge. We are watching your style, cadence, and how you handle a real conversation. After that, we sit down together and talk about the role.
We hire when the right person shows up.
Benefits
· Casual dress
· Dental care
· Extended health care
· Life insurance
· Paid time off
· Vision care
· Hybrid remote in Calgary, AB
Pay: $50,000.00-$180,000.00 per year
Benefits:
- Casual dress
- Company events
- Dental care
- Employee assistance program
- Extended health care
- Paid time off
- Vision care
- Work from home
Work Location: In person
