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Microsoft Help Desk Remote Jobs in Calgary, AB (NOW HIRING)

Wing Assistant

GTM Sales

Calgary, AB · Remote

We help companies get high-quality support across roles like executive assistance, admin support ... Educate prospects who may not have considered remote assistants, virtual assistants, offshore ...

Bulletproof IT

Support Specialist - Calgary

Calgary, AB · On-site +1

Are you passionate about IT and helping humans get the most from their technology? * Do you want to ... Microsoft Exchange/365 * Remote Desktop Services * Advanced firewalls * Cloud services * Mobile ...

Bentley Systems

Associate Consultant

Calgary, AB · On-site +1

... well as remote colleagues globally. This role offers an excellent opportunity to build your ... Proficient in use of the Microsoft Office Suite (Word, Excel, PowerPoint, Visio, and SharePoint ...

WSP

Intermediate Spatial Ecologist

Calgary, AB · On-site +1

CA$43.90 - CA$60.40/hr

In this role, you will help integrate emerging technologies-including artificial intelligence (AI ... Integrate remote sensing datasets, including satellite imagery, LiDAR, UAV/drone imagery, and Earth ...

WSP

Intermediate Spatial Ecologist

Calgary, AB · On-site +1

CA$43.90 - CA$60.40/hr

In this role, you will help integrate emerging technologies-including artificial intelligence (AI ... Integrate remote sensing datasets, including satellite imagery, LiDAR, UAV/drone imagery, and Earth ...

Enerflex Ltd.

Manager, IT Security

Calgary, AB · On-site +1

As Manager, IT Security, you will lead a capable team, strengthen security practices, and help ... Microsoft 365, identity, privileged access, conditional access, remote access, encryption, data ...

International SOS

Registered Nurse

Calgary, AB · Remote

... help organisations fulfil their Duty of Care responsibilities. Now, we're looking for talented ... Community health nursing in remote Indigenous communities isn't just a job-it's an opportunity to ...

True Environmental

Manager - Hydrogeology

Calgary, AB · On-site +1

CA$120K - CA$180K/yr

Remote - Regular-Full Time As the Supervisor - Hydrogeology, this role will be responsible for ... Proficiency in Microsoft Office Suite (Excel, Word, PowerPoint) and other business software

Quadbridge

Account Manager

Calgary, AB · Remote

CA$60K - CA$80K/yr

  • Medical

  • Dental

  • Life

Knowledge of Microsoft products and technologies, an asset Why Quadbridge? * Invest in Your Future ... Monday to Friday, 8:30am-5pm, Remote Fulltime, Permanent Salary/Wage Range: $60,000-$80,000 per ...

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All JobsMicrosoft Help Desk JobsMicrosoft Help Desk Remote JobsMicrosoft Help Desk Remote Jobs in Calgary, AB

Microsoft Help Desk Remote information

What is a Microsoft Help Desk Remote?

Microsoft Help Desk Remote jobs involve providing technical support and troubleshooting assistance to users of Microsoft products and services, such as Windows, Office, and Microsoft 365, from a remote location. Employees in these roles typically handle customer inquiries, resolve software or hardware issues, and guide users through problem-solving steps via phone, chat, or email. These positions require strong communication skills, technical knowledge of Microsoft products, and the ability to work independently from home or another remote setting.

What skills and qualifications are needed to thrive as a Microsoft Help Desk Remote specialist?

To thrive as a Microsoft Help Desk Remote specialist, you need a solid understanding of Windows operating systems, Microsoft Office applications, troubleshooting techniques, and often an associate degree or relevant certification such as CompTIA A+ or Microsoft Certified: Modern Desktop Administrator Associate. Familiarity with remote support tools, ticketing systems like ServiceNow or Zendesk, and knowledge of Active Directory are typically required. Exceptional communication, patience, and problem-solving skills help you efficiently assist users and resolve technical issues from a distance. These abilities are crucial for providing timely, effective support and ensuring user satisfaction in a remote IT environment.

What are some typical challenges faced by remote Microsoft Help Desk professionals, and how can they effectively address them?

Remote Microsoft Help Desk professionals often encounter challenges such as troubleshooting technical issues without physical access to devices, managing multiple support requests simultaneously, and maintaining clear communication with users who may have varying levels of technical knowledge. To address these challenges, leveraging remote diagnostic tools, setting clear expectations with users, and utilizing knowledge bases or documentation can be highly effective. Additionally, regular collaboration with team members through chat or video meetings helps ensure consistent support quality and knowledge sharing.

What is the difference between Microsoft Help Desk Remote vs Technical Support Specialist?

AspectMicrosoft Help Desk RemoteTechnical Support Specialist
CertificationsCompTIA A+, Microsoft Certified Desktop Support Technician (MCDST)CompTIA A+, HDI Support Center Analyst
Work EnvironmentRemote, help desk or call center settingOn-site or remote, technical support roles in various industries
Industry UsageIT support, software companies, tech service providersIT, telecommunications, hardware/software companies

Microsoft Help Desk Remote and Technical Support Specialist roles share similar certifications and work environments, often involving remote support for software and hardware issues. However, Microsoft Help Desk Remote positions are typically focused on supporting Microsoft products specifically, while Technical Support Specialists may handle a broader range of technologies and on-site support. Both roles are essential in IT support, but the Microsoft Help Desk Remote role emphasizes Microsoft expertise and remote troubleshooting skills.

What are popular job titles related to Microsoft Help Desk Remote jobs in Calgary, AB?

For Microsoft Help Desk Remote jobs in Calgary, AB, the most frequently searched job titles are:

What job categories do people searching Microsoft Help Desk Remote jobs in Calgary, AB look for?

The top searched job categories for Microsoft Help Desk Remote jobs in Calgary, AB are:

Microsoft Help Desk Remote jobs near you
Infographic showing various Microsoft Help Desk Remote job openings in Calgary, AB as of August 2026, with employment types broken down into 1% As Needed, 71% Full Time, 24% Part Time, and 4% Contract. Highlights an 85% Physical, 3% Hybrid, and 12% Remote job distribution.

GTM Sales

Wing Assistant

Calgary, AB • Remote

Full-time

Re-posted 16 days ago

Job description

Wing Assistant is building the next generation of AI-enabled workforce solutions for growing businesses. We help companies get high-quality support across roles like executive assistance, admin support, customer support, sales support, recruiting support, operations support, and other business functions.

Our growth depends on a steady flow of qualified opportunities, and we are hiring a Go-to-Market Associate to help create them. This person will sit at the front line of our revenue motion: identifying companies with active hiring needs, reaching out with a compelling alternative to traditional hiring, and booking qualified meetings for our sales team.

This is a high-energy, high-ownership role for someone early in their career who wants to learn fast, build real outbound skills, and grow into bigger roles across sales, growth, revenue, or go-to-market strategy over time.

It is a great fit for someone who is competitive, well-organized, motivated by clear targets, and genuinely curious about how AI, remote talent, and global workforce solutions are changing the way companies build teams.

What You'll Do

Generate Qualified Opportunities

  • Identify companies actively hiring for roles Wing can support, such as Executive Assistants, Admin Assistants, Customer Support, Sales Support, Recruiting Support, Operations Support, and other business support roles.
  • Use job postings, hiring signals, company growth signals, and account research to find strong-fit prospects.
  • Research target accounts to understand what they are hiring for, why they may need support, and where Wing could be a strong fit.
  • Reach out to prospective customers across email, phone, LinkedIn, and other outbound channels.
  • Run focused outbound campaigns around active hiring needs, operational pain points, and alternative workforce solutions.
  • Hold early discovery conversations to understand a prospect's hiring needs, pain points, urgency, and openness to remote talent or AI-enabled workforce solutions.
  • Communicate what Wing Assistant does and why it matters clearly enough to earn the next meeting.
  • Book qualified appointments with companies that have a clear hiring need, relevant business use case, or strong fit for Wing.

Turn Hiring Intent Into Conversations

  • Monitor companies that are posting roles Wing can service.
  • Understand what the company is likely trying to solve by hiring that role.
  • Position Wing as a faster, more flexible, and more scalable alternative to traditional hiring.
  • Educate prospects who may not have considered remote assistants, virtual assistants, offshore talent, or AI-enabled workforce support before.
  • Create curiosity with founders, executives, operators, HR leaders, recruiting teams, and department heads.

Support the Revenue Team

  • Work closely with the sales team to build and protect a healthy, well-qualified pipeline.
  • Hand off opportunities cleanly, with the context needed to move conversations forward.
  • Share key details from discovery calls, including the role the company is hiring for, their current hiring process, pain points, timing, budget signals, and decision-makers involved.
  • Keep activity, notes, and pipeline data accurate and current in our CRM.

Bring the Market Back In

  • Feed what you are hearing from prospects back to the Sales, Marketing, and Product teams.
  • Help refine messaging and outreach based on what is actually landing with companies.
  • Identify patterns in hiring demand, objections, industries, and roles where Wing is resonating.
  • Suggest new outbound angles based on job postings, hiring trends, and prospect conversations.
What We're Looking For

Core Requirements

  • 1 to 4+ years in sales, appointment setting, cold calling, recruiting, staffing, lead generation, outbound marketing, growth, or a comparable role.
  • A real interest in go-to-market strategy, pipeline generation, and B2B growth.
  • Proven background in prospecting, cold calling, appointment setting, or high-volume outbound outreach.
  • Strong written and verbal communication; you can get to the point and make it compelling.
  • Comfort reaching out to companies that may not have considered remote assistants, virtual assistants, offshore talent, or AI-enabled workforce solutions before.
  • Strong research skills and the ability to turn hiring signals into relevant outbound messaging.
  • Strong organization and the resilience to keep going when a day does not go your way.
  • The drive that comes from chasing clear goals, activity metrics, and booked meeting targets.
  • The ability to run your own desk while still collaborating well across teams.
  • A genuine eagerness to learn the product, the market, and the craft of go-to-market execution quickly.
 

Nice to Have

  • Exposure to staffing companies, recruiting firms, BPOs, outsourcing companies, virtual assistant companies, digital agent companies, or high-ticket professional services organizations.
  • Familiarity with CRM and sales engagement tools such as HubSpot, Salesforce, Outreach, Salesloft, Apollo, Instantly, Clay, Close, or LinkedIn Sales Navigator.
  • Familiarity with auto dialers, power dialers, cold calling workflows, and high-volume outbound systems.
  • Experience prospecting into founders, executives, operations leaders, HR leaders, recruiting teams, customer support leaders, sales leaders, or department heads.
  • Awareness of business support workflows such as executive assistance, admin support, sales support, customer support, recruiting coordination, inbox/calendar management, and back-office operations.
$1,200 - $2,500 a month

In addition to base compensation, this role includes performance-based incentives tied to qualified meetings, sales outcomes, and weekly activity targets.

Appointment and Deal Bonuses

  • Earn a bonus for every qualified meeting that shows up.
  • Earn an additional bonus when a qualified meeting turns into a closed customer.

This means you are rewarded not just for booking activity, but for creating real opportunities that move through the revenue process.

Weekly Competitions

We also run weekly competitions to keep the team competitive, motivated, and focused on the right activity metrics.

  • Weekly bonus opportunity for top dial activity.
  • Weekly bonus opportunity for top meeting production.

These incentives are designed for people who are driven by targets, enjoy competition, and want direct upside from their effort.

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.
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