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Virtual Assistant Assistant Jobs in Ontario (NOW HIRING)

Wing Assistant

GTM Sales Associate

Toronto, ON · 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 ...

Zirtual

Remote Virtual Executive Assistant

Hearst, ON

CA$1.5K - CA$3.8K/mo

The Executive Assistant is a vital member of the Zirtual team and serves as the primary point of ... Coordinate virtual and in-person meetings or events Operations & Task Management * Support day-to ...

Zirtual

Remote Virtual Executive Assistant

Dryden, ON · On-site

CA$1.5K - CA$3.8K/mo

The Executive Assistant is a vital member of the Zirtual team and serves as the primary point of ... Coordinate virtual and in-person meetings or events Operations & Task Management * Support day-to ...

VON Canada (Ontario)

You are invited to attend one of our upcoming Virtual Job Fairs, attendance is free! This will be a ... Continuing Care Assistant (CCA) * Registered Nurse (RN) * Licensed Practical Nurse (LPN) * And many ...

VON Canada (Ontario)

VON Virtual Job Fair

Brantford, ON · On-site

You are invited to attend one of our upcoming Virtual Job Fairs, attendance is free! This will be a ... Continuing Care Assistant (CCA) * Registered Nurse (RN) * Licensed Practical Nurse (LPN) * And many ...

VON Canada (Ontario)

VON Virtual Job Fair

Sarnia, ON · On-site

You are invited to attend one of our upcoming Virtual Job Fairs, attendance is free! This will be a ... Continuing Care Assistant (CCA) * Registered Nurse (RN) * Licensed Practical Nurse (LPN) * And many ...

Zirtual

Remote Virtual Executive Assistant

Sandy Lake, ON · On-site

CA$1.5K - CA$3.8K/mo

The Executive Assistant is a vital member of the Zirtual team and serves as the primary point of ... Coordinate virtual and in-person meetings or events Operations & Task Management * Support day-to ...

VON Canada (Ontario)

VON Virtual Job Fair

North Bay, ON · On-site

You are invited to attend one of our upcoming Virtual Job Fairs, attendance is free! This will be a ... Continuing Care Assistant (CCA) * Registered Nurse (RN) * Licensed Practical Nurse (LPN) * And many ...

VON Canada (Ontario)

VON Virtual Job Fair

Tobermory, ON · On-site

You are invited to attend one of our upcoming Virtual Job Fairs, attendance is free! This will be a ... Continuing Care Assistant (CCA) * Registered Nurse (RN) * Licensed Practical Nurse (LPN) * And many ...

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Virtual Assistant Assistant information

How to get work as a virtual assistant assistant?

To get work as a virtual assistant assistant, you should develop strong organizational and communication skills, familiarize yourself with common tools like email, calendar management, and project management software, and create a professional online presence through platforms such as Upwork or Fiverr. Building a portfolio of relevant experience and obtaining certifications in administrative support can also improve your chances of securing work.

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

AspectVirtual Assistant AssistantVirtual Assistant
CredentialsBasic administrative skills, possibly some certifications in office softwareSame as Virtual Assistant, often with additional specialized skills
Work EnvironmentRemote, home-based or freelanceRemote, home-based or freelance
Employer & IndustryBusinesses, entrepreneurs, online companiesBusinesses, entrepreneurs, online companies
Common Search IntentComparing support roles, entry-level virtual supportGeneral virtual support services, more experienced tasks

The Virtual Assistant Assistant typically performs basic administrative tasks similar to a Virtual Assistant but may focus on more specific or entry-level support roles. Both roles are remote, require similar skills, and are used across various industries. The main difference lies in the scope and complexity of tasks, with the Virtual Assistant often handling a broader range of responsibilities.

How do I start working as a virtual assistant?

To start working as a virtual assistant, you should develop relevant skills such as organization, communication, and proficiency with tools like email, calendar management, and office software. Creating a professional profile on freelance platforms and applying for entry-level positions can help you find opportunities; some roles may require basic certifications or experience in administrative tasks.

How do you become a virtual assistant from home?

To become a virtual assistant from home, you should develop relevant skills such as organization, communication, and proficiency with tools like email, calendar management, and office software. Gaining experience through freelance platforms or online courses can help build your portfolio, and establishing a reliable internet connection and a dedicated workspace are essential for remote work.
What are popular job titles related to Virtual Assistant Assistant jobs in Ontario? For Virtual Assistant Assistant jobs in Ontario, the most frequently searched job titles are:
What job categories do people searching Virtual Assistant Assistant jobs in Ontario look for? The top searched job categories for Virtual Assistant Assistant jobs in Ontario are:
What cities in Ontario are hiring for Virtual Assistant Assistant jobs? Cities in Ontario with the most Virtual Assistant Assistant job openings:
Virtual Assistant Assistant jobs near you
Infographic showing various Virtual Assistant Assistant job openings in Ontario as of July 2026, with employment types broken down into 1% As Needed, 76% Full Time, 20% Part Time, 1% Temporary, and 2% Contract. Highlights an 94% Physical, 3% Hybrid, and 3% Remote job distribution.

GTM Sales Associate

Wing Assistant

Toronto, ON • Remote

Full-time

Re-posted yesterday

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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