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Senior Remote Virtual Assistant Jobs in Calgary, AB

Wing Assistant

GTM Sales

Calgary, AB · Remote

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 ...

HMG Careers

Remote Sales Specialist

Calgary, AB · Remote

CA$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers ... schedule virtual meetings with clients * Present benefit programs and assist clients with ...

HMG Careers

Remote Sales Specialist

Calgary, AB · Remote

CA$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers ... schedule virtual meetings with clients * Present benefit programs and assist clients with ...

HMG Careers

Remote Sales Specialist

Airdrie, AB · Remote

CA$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers ... schedule virtual meetings with clients * Present benefit programs and assist clients with ...

Globe Life Insurance

Be Seen First

Remote Customer Sales and Support Representative (Entry-Level)

Calgary, AB · Remote

CA$60K - CA$80K/yr

During scheduled virtual conversations, you'll listen to their needs, provide clear information ... Respond to questions with professionalism and care * Assist with completing applications and ...

Tetra Tech

Senior Civil Structural Engineer

Calgary, AB · On-site +1

Work remote and at our great office location, right in the heart of downtown Calgary. * Flexibility ... Tetra Tech may use AI-enabled tools to screen, assess, and assist in selecting applicants for this ...

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Senior Remote Virtual Assistant information

What is the difference between Senior Remote Virtual Assistant vs Virtual Assistant?

AspectSenior Remote Virtual AssistantVirtual Assistant
CredentialsExperience, advanced skills, possibly certificationsBasic skills, entry-level experience
Work EnvironmentRemote, independent, often handling complex tasksRemote, administrative support tasks
Employer UsageBusinesses seeking experienced support for specialized tasksStartups, small businesses, entrepreneurs
Search IntentAdvanced virtual assistance, senior virtual assistant rolesVirtual assistant jobs, entry-level virtual support

The main difference between a Senior Remote Virtual Assistant and a Virtual Assistant lies in experience, skill level, and task complexity. Senior Virtual Assistants typically handle more complex, specialized tasks and may have certifications or extensive experience, whereas Virtual Assistants often perform basic administrative duties. Both roles are remote and support businesses, but the senior role is suited for more experienced professionals seeking advanced responsibilities.

How does a Senior Remote Virtual Assistant typically collaborate with clients and team members across different time zones?

As a Senior Remote Virtual Assistant, effective collaboration across time zones involves using digital communication tools like email, instant messaging, and project management platforms to stay connected with clients and colleagues. Scheduling regular check-ins and setting clear expectations for response times help ensure smooth workflow and timely project delivery. Flexibility and proactive communication are key, as you may need to adjust your working hours for important meetings or deadlines. Building strong organizational skills and maintaining up-to-date records of tasks also support seamless teamwork in a remote environment.

What are Senior Remote Virtual Assistants?

Senior Remote Virtual Assistants are highly experienced professionals who provide administrative, technical, or creative support to businesses or executives from a remote location. They handle a variety of tasks such as calendar management, email correspondence, travel arrangements, and project coordination, often with minimal supervision. As 'senior' assistants, they typically manage more complex tasks, mentor junior assistants, and may oversee entire virtual teams. Their expertise allows them to streamline processes, improve efficiency, and support high-level decision-making. This role is ideal for those with excellent organizational, communication, and problem-solving skills.

What are the key skills and qualifications needed to thrive as a Senior Remote Virtual Assistant, and why are they important?

To thrive as a Senior Remote Virtual Assistant, you need advanced organizational skills, multitasking abilities, and several years of administrative experience, often supported by a relevant degree or certifications. Proficiency with productivity tools such as Microsoft Office, Google Workspace, project management software, and communication platforms like Slack or Zoom is essential. Exceptional communication, proactivity, and problem-solving skills help you excel in remote settings and manage tasks independently. These competencies are vital for efficiently supporting executives or teams, ensuring seamless operations, and maintaining high productivity from a remote environment.
What are popular job titles related to Senior Remote Virtual Assistant jobs in Calgary, AB? For Senior Remote Virtual Assistant jobs in Calgary, AB, the most frequently searched job titles are:
What job categories do people searching Senior Remote Virtual Assistant jobs in Calgary, AB look for? The top searched job categories for Senior Remote Virtual Assistant jobs in Calgary, AB are:
Senior Remote Virtual Assistant jobs near you
Infographic showing various Senior Remote Virtual Assistant job openings in Calgary, AB as of July 2026, with employment types broken down into 59% Full Time, 18% Part Time, and 23% Contract. Highlights an 100% Remote job distribution.
GTM Sales

GTM Sales

Wing Assistant

Calgary, AB • Remote

Full-time

Posted 23 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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