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Virtual Assistant Manager Jobs in Ontario (NOW HIRING)

Wing Assistant

GTM Sales Associate

Toronto, ON · Remote

... virtual assistant companies, digital agent companies, or high-ticket professional services organizations. * Familiarity with CRM and sales engagement tools such as HubSpot, Salesforce, Outreach ...

Foot Locker

Assistant Manager

Toronto, ON

CA$23.10/hr

Assistant Managers are handson leaders who move with urgency, stay connected to customers and ... Cameras must be on for all virtual interviews. * AI tools are strictly prohibited during interviews ...

Foot Locker

Assistant Manager

Toronto, ON · On-site

CA$23.10/hr

Assistant Managers are handson leaders who move with urgency, stay connected to customers and ... Cameras must be on for all virtual interviews. * AI tools are strictly prohibited during interviews ...

Foot Locker

Assistant Manager

Windsor, ON · On-site

CA$23.10/hr

Assistant Managers are handson leaders who move with urgency, stay connected to customers and ... Cameras must be on for all virtual interviews. * AI tools are strictly prohibited during interviews ...

Foot Locker

Assistant Manager

Saint Catharines, ON · On-site

CA$23.10/hr

Assistant Managers are handson leaders who move with urgency, stay connected to customers and ... Cameras must be on for all virtual interviews. * AI tools are strictly prohibited during interviews ...

Foot Locker

Assistant Manager

Ottawa, ON · On-site

CA$23.10/hr

Assistant Managers are handson leaders who move with urgency, stay connected to customers and ... Cameras must be on for all virtual interviews. * AI tools are strictly prohibited during interviews ...

Foot Locker

Assistant Manager

Sudbury, ON · On-site

CA$23.10/hr

Assistant Managers are handson leaders who move with urgency, stay connected to customers and ... Cameras must be on for all virtual interviews. * AI tools are strictly prohibited during interviews ...

Foot Locker

Assistant Manager

London, ON · On-site

CA$20.85/hr

Assistant Managers are handson leaders who move with urgency, stay connected to customers and ... Cameras must be on for all virtual interviews. * AI tools are strictly prohibited during interviews ...

Foot Locker

Assistant Manager

Burlington, ON · On-site

CA$23.10/hr

Assistant Managers are handson leaders who move with urgency, stay connected to customers and ... Cameras must be on for all virtual interviews. * AI tools are strictly prohibited during interviews ...

Zirtual

Remote Virtual Executive Assistant

Dryden, ON · On-site

CA$1.5K - CA$3.8K/mo

Manage and coordinate complex calendars and appointments * Schedule meetings, calls, and events ... Coordinate virtual and in-person meetings or events Operations & Task Management * Support day-to ...

Zirtual

Remote Virtual Executive Assistant

Hearst, ON · On-site

CA$1.5K - CA$3.8K/mo

Manage and coordinate complex calendars and appointments * Schedule meetings, calls, and events ... Coordinate virtual and in-person meetings or events Operations & Task Management * Support day-to ...

Zirtual

Remote Virtual Executive Assistant

Sandy Lake, ON · On-site

CA$1.5K - CA$3.8K/mo

Manage and coordinate complex calendars and appointments * Schedule meetings, calls, and events ... Coordinate virtual and in-person meetings or events Operations & Task Management * Support day-to ...

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Virtual Assistant Manager information

What are the key skills and qualifications needed to thrive as a virtual assistant manager, and why are they important?

To thrive as a Virtual Assistant Manager, you need strong organizational skills, experience in remote team supervision, and a background in administration or business management. Familiarity with project management tools like Asana or Trello, video conferencing platforms, and cloud-based document systems is typically required. Excellent communication, problem-solving abilities, and adaptability help you excel in leading distributed teams and addressing client needs. These skills ensure efficient workflow coordination, clear virtual collaboration, and high-quality client service in a remote work environment.

What are some common challenges faced by virtual assistant managers when overseeing remote teams, and how can they be addressed?

Virtual Assistant Managers often encounter challenges such as coordinating tasks across different time zones, maintaining clear communication, and fostering team engagement remotely. To address these, it's essential to implement effective project management tools, establish regular check-ins, and set clear expectations for deliverables. Building a sense of community through virtual team-building activities and providing ongoing feedback can also enhance collaboration and productivity in a remote environment.

What is a virtual assistant manager?

Virtual Assistant Managers are professionals who oversee and coordinate teams of virtual assistants, ensuring efficient workflow and high-quality support services for clients or organizations. They are responsible for assigning tasks, monitoring performance, providing training, and resolving issues that arise within the team. Virtual Assistant Managers often work remotely themselves and utilize digital tools to manage communication and productivity. Their role is essential in maintaining organization, meeting deadlines, and ensuring client satisfaction in a virtual work environment.
What are popular job titles related to Virtual Assistant Manager jobs in Ontario? For Virtual Assistant Manager jobs in Ontario, the most frequently searched job titles are:
What job categories do people searching Virtual Assistant Manager jobs in Ontario look for? The top searched job categories for Virtual Assistant Manager jobs in Ontario are:
What cities in Ontario are hiring for Virtual Assistant Manager jobs? Cities in Ontario with the most Virtual Assistant Manager job openings:
Virtual Assistant Manager jobs near you
Infographic showing various Virtual Assistant Manager job openings in Ontario as of August 2026, with employment types broken down into 86% Full Time, and 14% Contract. Highlights an 74% In-person, and 26% Remote job distribution.

GTM Sales Associate

Wing Assistant

Toronto, ON • Remote

Full-time

Re-posted 6 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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