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Remote 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 ...

Wing Assistant

Web Presence Specialist

Toronto, ON · Remote

CA$110K - CA$135K/yr

About Us Wing Assistant is one of the world's largest virtual talent companies. We are a venture-backed scaleup, based in Silicon Valley, but operate fully remote. Wing is scaling rapidly, and ...

Wing Assistant

Website Manager

Toronto, ON · Remote

CA$110K - CA$135K/yr

About Us Wing Assistant is one of the world's largest virtual talent companies. We are a venture-backed scaleup, based in Silicon Valley, but operate fully remote. Wing is scaling rapidly, and ...

#twiceasnice Recruiting

Support customer communications and presentations * Assist with social media and marketing efforts [REMOTE] Sales & Operations Coordinator Qualifications * 3+ years of B2B sales support or similar ...

HMG Careers

Remote Sales Specialist

North Bay, ON · Remote

CA$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers ... Present benefit programs and assist clients with enrollment * Build and maintain strong client ...

HMG Careers

Remote Sales Specialist

ON · Remote

CA$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers ... Present benefit programs and assist clients with enrollment * Build and maintain strong client ...

HMG Careers

Remote Sales Specialist

Markham, ON · Remote

CA$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers ... Present benefit programs and assist clients with enrollment * Build and maintain strong client ...

HMG Careers

Remote Sales Specialist

Oakville, ON · Remote

CA$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers ... Present benefit programs and assist clients with enrollment * Build and maintain strong client ...

HMG Careers

Remote Sales Specialist

Thunder Bay, ON · Remote

CA$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers ... Present benefit programs and assist clients with enrollment * Build and maintain strong client ...

HMG Careers

Remote Sales Specialist

Burlington, ON · Remote

CA$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers ... Present benefit programs and assist clients with enrollment * Build and maintain strong client ...

HMG Careers

Remote Sales Specialist

Oshawa, ON · Remote

CA$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers ... Present benefit programs and assist clients with enrollment * Build and maintain strong client ...

HMG Careers

Remote Sales Specialist

ON · Remote

CA$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers ... Present benefit programs and assist clients with enrollment * Build and maintain strong client ...

HMG Careers

Remote Sales Specialist

Mississauga, ON · Remote

CA$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers ... Present benefit programs and assist clients with enrollment * Build and maintain strong client ...

HMG Careers

Remote Sales Specialist

Guelph, ON · Remote

CA$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers ... Present benefit programs and assist clients with enrollment * Build and maintain strong client ...

HMG Careers

Remote Sales Specialist

Oshawa, ON · Remote

CA$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers ... Present benefit programs and assist clients with enrollment * Build and maintain strong client ...

HMG Careers

Remote Sales Specialist

Vaughan, ON · Remote

CA$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers ... Present benefit programs and assist clients with enrollment * Build and maintain strong client ...

HMG Careers

Remote Sales Specialist

Burlington, ON · Remote

CA$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers ... Present benefit programs and assist clients with enrollment * Build and maintain strong client ...

HMG Careers

Remote Sales Specialist

Richmond Hill, ON · Remote

CA$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers ... Present benefit programs and assist clients with enrollment * Build and maintain strong client ...

HMG Careers

Remote Sales Specialist

Barrie, ON · Remote

CA$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers ... Present benefit programs and assist clients with enrollment * Build and maintain strong client ...

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Remote Assistant information

What is a Remote Assistant?

A Remote Assistant is a professional who provides administrative, technical, or creative support to businesses or individuals from a remote location. Their duties may include managing emails, scheduling appointments, data entry, customer service, social media management, and more. Remote Assistants use digital communication tools to collaborate with their employers, making this role ideal for flexible, location-independent work. This position is often referred to as a Virtual Assistant, and is popular among freelancers and remote workers.

What is the difference between Remote Assistant vs Virtual Assistant?

AspectRemote AssistantVirtual Assistant
CredentialsOften no formal certification required, but administrative or technical skills preferredTypically no formal certification, but administrative, communication, and technical skills are common
Work EnvironmentRemote, often part-time or freelance, working from home or any locationRemote, usually freelance or contracted, working from home or remote offices
Employer & Industry UsageUsed across various industries for administrative support, customer service, or technical tasksCommonly used in administrative, marketing, and customer service sectors for support tasks
Search & Comparison IntentPeople compare to Virtual Assistant to understand scope, tasks, and flexibility

Both Remote Assistants and Virtual Assistants work remotely providing administrative or support services. While their roles overlap significantly, Remote Assistants may sometimes handle more technical or specialized tasks, depending on their skills. Understanding these differences helps job seekers and employers find the right fit for their needs.

How can I make 2000 a week working from home?

Remote assistants can earn $2000 a week by taking on multiple clients, specializing in high-demand tasks like administrative support or social media management, and developing strong organizational and communication skills. Building a reputation through consistent quality work and using platforms like Upwork or Fiverr can help secure higher-paying projects. Increasing your hourly rate and working full-time hours are also key strategies.

What Does a Remote Assistant Do?

Remote assistants provide support to staff and executives at a company. Some organizations use remote assistants as customer service agents who are the first point of contact for clients when they call in for information on products or services. Many remote assistants work exclusively with managers and executives, but some are assigned to help specific teams or departments. As a remote assistant, you may help schedule meetings, coordinate travel arrangements, assign tasks, respond to calls and emails, and set up appointments. You may be required to use virtual office software to coordinate with other employees and prioritize job duties with varying deadlines. If you work for an international company, you may be asked to work unusual hours to provide support to employees around the world in different time zones.

How do Remote Assistants effectively manage communication across different time zones within a distributed team?

Remote Assistants often support teams and clients located around the world, which can make coordinating schedules and real-time communication challenging. Most successful Remote Assistants rely on clear protocols, such as shared calendars, regular check-ins, and asynchronous communication tools like email and project management platforms. It's important to proactively clarify preferred communication windows and establish expectations for response times. This approach helps ensure smooth collaboration and minimizes miscommunication, even when team members are not online simultaneously.

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

To thrive as a Remote Assistant, you need strong organizational skills, attention to detail, and proficiency in administrative tasks, often supported by prior experience or a relevant diploma. Familiarity with productivity tools such as Microsoft Office, Google Workspace, project management software, and communication platforms like Slack or Zoom is typically required. Excellent time management, self-motivation, and effective written and verbal communication help you stand out in this remote role. These skills and qualities are crucial for efficiently supporting clients or teams from a distance and ensuring seamless virtual operations.

How do I become a remote virtual assistant?

To become a remote virtual assistant, you should develop strong organizational, communication, and computer skills, and become familiar with tools like email, calendar management, and project management software. Gaining relevant experience or certifications can improve your prospects, and setting up a dedicated workspace helps establish professionalism. Many virtual assistants find work through freelance platforms or job boards that specialize in remote roles.

How to make $1000 a week remotely?

A remote assistant can earn $1000 a week by offering specialized administrative, customer service, or technical support services, often through freelance platforms or direct clients. Increasing income may involve gaining relevant skills, certifications, or experience, and working multiple clients or projects simultaneously to reach higher weekly earnings.

Does Amazon hire virtual assistants?

Amazon does not typically hire virtual assistants as a formal job position; however, some third-party sellers and Amazon services may employ virtual assistants to handle tasks like customer service, product listing, and order management. These roles are often freelance or contract-based and require skills in communication, organization, and familiarity with tools like spreadsheets and e-commerce platforms.
More about Remote Assistant jobs
What are the most commonly searched types of Remote jobs in Ontario? The most popular types of Remote jobs in Ontario are:
What are popular job titles related to Remote Assistant jobs in Ontario? For Remote Assistant jobs in Ontario, the most frequently searched job titles are:
What job categories do people searching Remote Assistant jobs in Ontario look for? The top searched job categories for Remote Assistant jobs in Ontario are:
What cities in Ontario are hiring for Remote Assistant jobs? Cities in Ontario with the most Remote Assistant job openings:
Remote Assistant jobs near you
Infographic showing various Remote Assistant job openings in Ontario as of July 2026, with employment types broken down into 1% As Needed, 80% Full Time, 16% Part Time, 1% Temporary, and 2% Contract. Highlights an 98% Physical, 1% Hybrid, and 1% Remote job distribution.
GTM Sales Associate

GTM Sales Associate

Wing Assistant

Toronto, ON • Remote

Full-time

Posted 22 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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