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Remote Appointment Setting 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 ... Proven background in prospecting, cold calling, appointment setting, or high-volume outbound ...

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Remote Appointment Setting information

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How much do remote appointment setting jobs pay per hour?

As of Aug 8, 2026, the average hourly pay for remote appointment setting in Ontario is $20.43, according to ZipRecruiter salary data. Most workers in this role earn between $13.22 and $20.43 per hour, depending on experience, location, and employer.

What skills and qualifications are needed for remote appointment setting?

To thrive as a Remote Appointment Setter, you need excellent verbal communication, organizational skills, and experience with customer service or telemarketing. Familiarity with CRM software, scheduling tools, and phone systems is often required to efficiently manage leads and track follow-ups. Strong self-motivation, time management, and professionalism help individuals stand out in this remote role. These skills are crucial for building rapport with clients, achieving set targets, and ensuring seamless appointment coordination from a distance.

What is a remote appointment setting?

A Remote Appointment Setting job involves contacting potential clients or leads to schedule appointments for sales representatives or business professionals. This role typically requires strong communication skills, the ability to handle objections, and proficiency in using CRM software or scheduling tools. It can be done from home, offering flexibility while playing a key role in generating business opportunities. Many industries, including sales, real estate, and healthcare, hire remote appointment setters to streamline their customer outreach efforts.

What challenges are faced in remote appointment setting, and how can they be managed?

A common challenge in Remote Appointment Setting is staying motivated and maintaining productivity without direct, in-person supervision. Distractions at home or managing different time zones can also impact scheduling efficiency. To overcome these challenges, it's helpful to establish a dedicated workspace, set daily goals, and use robust scheduling and CRM tools to keep tasks organized. Many teams provide regular virtual check-ins and support, which encourages collaboration and accountability. With discipline and the right tools, remote appointment setters can excel and enjoy a rewarding, flexible work environment.

How to become a remote appointment setting?

To become a remote appointment setter, you should develop strong communication and organizational skills, familiarize yourself with customer relationship management (CRM) tools, and have a reliable internet connection. Many roles require prior experience in sales or customer service and may prefer candidates with a high school diploma or equivalent. Applying through online job boards and demonstrating your ability to manage schedules and engage clients can help you secure a position.

How much do remote appointment setters make?

Remote appointment setters typically earn between $10 and $20 per hour, with some earning commissions or bonuses based on performance. Overall income depends on experience, industry, and the number of appointments scheduled, with many earning around $25,000 to $50,000 annually when including commissions.
What are the most commonly searched types of Appointment Setting jobs in Ontario? The most popular types of Appointment Setting jobs in Ontario are:
What are popular job titles related to Remote Appointment Setting jobs in Ontario? For Remote Appointment Setting jobs in Ontario, the most frequently searched job titles are:
What job categories do people searching Remote Appointment Setting jobs in Ontario look for? The top searched job categories for Remote Appointment Setting jobs in Ontario are:
What cities in Ontario are hiring for Remote Appointment Setting jobs? Cities in Ontario with the most Remote Appointment Setting job openings:
Remote Appointment Setting jobs near you
Infographic showing various Remote Appointment Setting job openings in Ontario as of August 2026, with employment types broken down into 2% As Needed, 76% Full Time, 16% Part Time, 1% Temporary, and 5% Contract. Highlights an 96% Physical, 1% Hybrid, and 3% Remote job distribution, with an average salary of $42,492 per year, or $20.4 per hour.

GTM Sales Associate

Wing Assistant

Toronto, ON • Remote

Full-time

Re-posted 5 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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