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 runs the technology behind around 80 businesses across Calgary, Edmonton, and Fernie. IT management, cybersecurity, Microsoft 365, and an AI services practice that is actually shipping work — all delivered through our BusinessOS framework. We have been doing this since 1991. We are not a sleepy MSP.
The opportunity
Calgary is full of 15 to 50-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 in Apollo 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 $3K MRR on your own — bigger or messier ones get handed to senior leadership and you stay on the deal
- Keep Pipedrive/Hubspot 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
- Conduct outbound calls and emails to prospective clients, primarily focusing on B2B sales opportunities
- Qualify inbound leads generated through marketing campaigns and outreach efforts
- Engage potential clients through telemarketing, leveraging strong communication skills to build rapport and understand their needs
- Develop and maintain a pipeline of qualified leads using Salesforce CRM and other sales tools
- Collaborate with the marketing team to execute targeted outreach strategies
- Assist in creating personalized pitches and presentations tailored to client needs
- Support business development initiatives by identifying new markets and opportunities
- Maintain detailed records of interactions, follow-ups, and client information within the CRM system
- Participate in ongoing training sessions to enhance product knowledge, sales techniques, and industry understanding
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
- 2 to 4 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. Spreadsheets are ok too … but we would like to move on.
- LinkedIn social selling that goes beyond a polished profile
- Ability to work independently as well as part of a team in a fast-paced environment
- Demonstrated ability to develop relationships with clients and manage multiple priorities effectively
- Excellent organizational skills with attention to detail
- A proactive attitude with a passion for sales and business growth
- You live in Calgary and you like being in the field
- Valid driver's license and a vehicle that starts in February
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, cybersecurity, or managed IT
- Your last job shows real progression, not just tenure
What you get from us
- Closing authority after a proven competence — we need to know who you are and built 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
- Promotion path that is 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) … we will talk about this a lot!
- Direct access to the President and senior leadership — we are not a place where good ideas die in a Slack channel
- Field-first culture — we care what you produce, not what time you showed up
What this job is not
- A desk job
- A place to coast
- A slow-moving corporate sales role with a 6-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 — 1 short paragraph, 10 – 15 sentences — on the best deal you ever closed. What it took, what you learned, what you would do differently. This is BRIEF … honestly … if you send in 2 paragraphs or more, you didn’t understand the assignment.
If we are interested … we will contact you to reach out to one of our team via email. This will be a cold email them on a product you want to sell. Could be anything. You want to get a reply with a time to connect for a phone call. That is the ask. From there a time for a phone call will be arranged and you will have 15 mins to pitch them. This is not to see what product knowledge you have, but a showcase of your style, cadence, and communication skills.
After that an interview time will arranged, There we can talk about the role and any questions we have for each other.
We hire when the right person shows up.
Pay: $31,200.00-$150,000.00 per year
Benefits:
- Casual dress
- Dental care
- Extended health care
- Life insurance
- Paid time off
- Vision care
- Work from home
Work Location: Hybrid remote in Calgary, AB T2E 7N7
