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Assistant Jobs in Ontario (NOW HIRING)

Wing Assistant

GTM Sales Associate

Toronto, ON · Remote

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 ...

Wing Assistant

Sales Enablement Trainer

Toronto, ON

CA$29K - CA$35K/yr

Wing Assistant is hiring a hands on Sales Enablement Trainer to level up our sales team - not with generic intro decks, but by improving the actual emails, calls, and cadences our reps use every day.

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 ...

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

Events Specialist

Toronto, ON

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 ...

Wing Assistant

Field & Events Marketer

Toronto, ON

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 ...

Cna

Senior Data Analytics Consultant

Toronto, ON · On-site

CA$90K - CA$105K/yr

At CNA, we strive to create a culture in which people know they matter and are part of something important, ensuring the abilities of all employees are used to their fullest potential. As part of the ...

TLC Laser Eye Centres

Clinical Assistant

Kitchener, ON · On-site

CA$19.55 - CA$22.22/hr

CLINICAL ASSISTANT | Kitchener, ON Working in a TLC Laser Eye Centres clinic (an affiliated entity of Vision Group) is to help improve people's eyesight. It is having the feeling of a mission ...

Linds & Associates

Legal Assistant

Toronto, ON

Legal Assistant Downtown Toronto Our client, a premier business law firm in Canada is in need of a recent graduate of the Legal Assistant or Law Clerk program to join its team working as a Legal ...

Linds & Associates

Legal Assistant

Toronto, ON

Legal Assistant Downtown Toronto Our client, a premier business law firm in Canada is in need of a recent graduate of the Legal Assistant or Law Clerk program to join its team working as a Legal ...

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All JobsAssistant JobsAssistant Jobs in Ontario

Assistant information

What are different types of assistants?

Assistants come in various forms, including executive assistants who support high-level managers, administrative assistants handling office tasks, virtual assistants providing remote support, and specialized assistants such as legal or medical assistants. Each type requires different skills, tools, and sometimes certifications, and they may work in office environments or remotely with flexible schedules.

What can I do as an assistant?

As an assistant, you can perform tasks such as managing schedules, organizing files, handling correspondence, and providing administrative support. The role often requires strong organizational skills, communication abilities, and proficiency with office software. Assistants may work in various settings including offices, healthcare, or legal environments, and some positions require specific certifications or experience.

What is the difference between Assistant vs Receptionist?

AspectAssistantReceptionist
Primary RoleSupports specific departments or executives with administrative tasksManages front desk, greets visitors, handles phone calls
Work EnvironmentOffice settings, often within teams or departmentsFront office, reception area, customer-facing roles
Required CredentialsHigh school diploma; sometimes additional certificationsHigh school diploma; customer service skills
Common UsageAssisting managers, executives, or teams with administrative supportHandling visitor inquiries, scheduling, and front desk operations

While both roles involve administrative tasks, assistants typically provide support to specific departments or individuals, whereas receptionists focus on front desk duties and visitor management. The assistant role often requires more specialized support skills, while receptionists primarily handle customer interactions and front office responsibilities.

What is an assistant?

Assistants are professionals who provide administrative, organizational, or personal support to individuals or teams within a company or organization. Their tasks can include managing schedules, handling correspondence, organizing meetings, preparing documents, and performing various clerical duties. Depending on the workplace, assistants may also help with research, travel arrangements, or basic project management. Their role is essential for ensuring that operations run smoothly and efficiently. Assistants often serve as the first point of contact and play a key part in facilitating communication and workflow.

How do assistants typically manage competing priorities and last-minute requests?

Assistants often juggle multiple tasks and must adapt quickly to shifting priorities, especially when supporting busy executives or teams. Effective time management, clear communication, and proactive organization are crucial for handling last-minute requests. Many Assistants rely on digital tools such as calendars, task managers, and communication platforms to stay organized and ensure nothing falls through the cracks. Building strong relationships with colleagues also helps in coordinating tasks and setting realistic expectations when urgent needs arise.

What kind of assistants make the most money?

Executive assistants and specialized assistants, such as legal or medical assistants, tend to earn the highest salaries among assistant roles due to their advanced skills and responsibilities. These positions often require additional certifications, experience, and proficiency with specific tools or software, which can contribute to higher pay.

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

To thrive as an Assistant, strong organizational abilities, time management, and proficiency in office procedures are essential, typically supported by a high school diploma or associate degree. Familiarity with office software like Microsoft Office Suite, calendar management tools, and basic bookkeeping systems is often required. Excellent communication, discretion, and adaptability are standout soft skills for this role. These competencies ensure efficient support to teams or executives, helping organizations operate smoothly and effectively.
More about Assistant jobs
What are popular job titles related to Assistant jobs in Ontario? For Assistant jobs in Ontario, the most frequently searched job titles are:
What job categories do people searching Assistant jobs in Ontario look for? The top searched job categories for Assistant jobs in Ontario are:
What cities in Ontario are hiring for Assistant jobs? Cities in Ontario with the most Assistant job openings:
Assistant jobs near you
Infographic showing various Assistant job openings in Ontario as of August 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

Wing Assistant

Toronto, ON • Remote

Full-time

Re-posted 4 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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